Summary.
This review covers the literature relating to asymmetric syntheses of pipecolic acid derivatives from 1997 to present. This review is organized according to the position and the degree of substitution of the piperidinic cycle. In a first section, syntheses of pipecolic acid itself are described. Then, successively, syntheses of C-3, C-4, C-5, C-6 substituted pipecolic acid derivatives are reported. Finally, syntheses of unsaturated pipecolic acid derivatives are presented before the last part devoted to the polysubstituted pipecolic acid derivatives.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Adams DR, Bailey PD, Collier ID, Heffernan JD, Stokes S (1996) An efficient route to the α-methyl ester of L-glutamic acid, and its conversion into cis-5-hydroxy-L-pipecolic acid. Chem Commun: 349–350
C Agami D Bihan L Hamon C Puchot-Kadouri (1998a) ArticleTitleThe tetraoxazinone way to enantiopure a-amino acids: synthesis of cis and trans 3-vinylpipecolic acids via an intramolecular reaction between an iminium ion and an allylsilane moieties. Tetrahedron 54 10309–10316 Occurrence Handle10.1016/S0040-4020(98)00486-4
Agami C, Bihan D, Hamon L, Kadouri-Puchot C, Lusinchi M (1998b) Enantioselective synthesis of an allenyl derivative of pipecolic acid. Eur J Org Chem: 2461–2465
C Agami C Kadouri-Puchot JC Kizirian (2000a) ArticleTitleA new enantioselective synthesis of (2S)-pipecolic acid. Synthetic Commun 30 2565–2572
C Agami S Comesse C Kadouri-Puchot (2000b) ArticleTitleAn efficient access to enantiomerically pure substituted derivatives of pipecolic acid. J Org Chem 65 4435–4439 Occurrence Handle10.1021/jo0000271
Agami C, Bisaro F, Comesse S, Guesné S, Kadouri-Puchot C, Morgentin R (2001) Asymmetric syntheses of enantiopure 4-substituted pipecolic acid derivatives. Eur J Org Chem: 2385–2389
C Agami S Comesse C Kadouri-Puchot (2002) ArticleTitleThe intriguing reactivity of functionalized β-amino alcohols with glyoxal: application to a new expedient enantioselective synthesis of trans-6-alkylpipecolic acids. J Org Chem 67 2424–2428 Occurrence Handle10.1021/jo010780+ Occurrence Handle11950283
M Andrei C Römming K Undheim (2004) ArticleTitleRh(II)-catalysed carbenoid cyclisations in a stereoselective approach to α-quaternary pipecolic acid derivatives. Tetrahedron: Asymm 15 1359–1370 Occurrence Handle10.1016/j.tetasy.2004.03.018
R Badorrey C Cativiela MD Díaz-de-Villegas JA Gálvez (1999) ArticleTitleStudy of the reaction of imines derived from (R)-glyceraldehyde with Danishefsky’s diene. Tetrahedron 55 7601–7612 Occurrence Handle10.1016/S0040-4020(99)00377-4
R Badorrey C Cativiela MD Díaz-de-Villegas JA Gálvez (2002) ArticleTitleHighly convergent stereoselective synthesis of chiral key intermediates in the synthesis of Palinavir from imines derived from L-glyceraldehyde. Tetrahedron 58 341–354 Occurrence Handle10.1016/S0040-4020(01)01152-8
J Barluenga F Aznar C Valdés C Ribas (1998) ArticleTitleEnantioselective synthesis of substituted pipecolic acid derivatives. J Org Chem 63 3918–3924 Occurrence Handle10.1021/jo9722414
L Battistini F Zanardi G Rassu P Spanu G Pelosi GG Fava MB Ferrari G Casiraghi (1997) ArticleTitleTotal synthesis of both enantiomers of trans-β-hydroxypipecolic acid. Tetrahedron: Asymm 8 2975–2987 Occurrence Handle10.1016/S0957-4166(97)00344-3
PL Beaulieu P Lavallée A Abraham PC Anderson C Boucher Y Bousquet JS Duceppe J Gillard V Gorys C Grand-Maitre L Grenier Y Guindon L Plamondon F Soucy S Valois D Wernic C Yoakim (1997) ArticleTitlePractical stereoselective synthesis of palinavir a potent HIV protease inhibitor. J Org Chem 64 3440–3448 Occurrence Handle10.1021/jo9702655
B Bellier S Da Nascimento H Meudal E Gincel BP Roques C Garbay (1998) ArticleTitleNovel constrained CCK-B dipeptoid antagonists derived from pipecolic acid. Bioorg Med Chem Lett 8 1419–1424 Occurrence Handle10.1016/S0960-894X(98)00231-5 Occurrence Handle9871777
R Bernasconi RSG Jones H Bittiger HR Olpe J Heid P Martin M Klein P Loo A Braunwalder M Schmutz (1986) ArticleTitleDoes pipecolic acid interact with the central GABA-ergic system? J Neural Transm 67 175–189 Occurrence Handle10.1007/BF01243346 Occurrence Handle3027250
MS Bodas P Kumar (2004) ArticleTitleAn asymmetric dihydroxylation route to (2S,3S)-3-hydroxypipecolic acid. Tetrahedron Lett 45 8461–8463 Occurrence Handle10.1016/j.tetlet.2004.09.123
DL Boger JH Chen KW Saionz (1996) ArticleTitleTotal synthesis and characterization of (−)-Sandramycin. DNA binding properties. J Am Chem Soc 118 1629–1644 Occurrence Handle10.1021/ja952799y
Y Bousquet PC Anderson T Bogri JS Duceppe L Grenier I Guse (1997) ArticleTitlePreparation of enantiopure 4-oxygenated pipecolic acid derivatives. Tetrahedron 53 15671–15680
CA Brooks DL Comins (2000) ArticleTitleAsymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid. Tetrahedron Lett 41 3551–3553 Occurrence Handle10.1016/S0040-4039(00)00460-3
MGP Buffat (2004) ArticleTitleSynthesis of piperidines. Tetrahedron 60 1701–1729 Occurrence Handle10.1016/j.tet.2003.11.043
JF Caplan R Zheng JS Blanchard JC Vederas (2000) ArticleTitleVinylogous amide analogues of diaminopimelic acid (DAP) as inhibitors of enzymes involved in bacterial lysine biosynthesis. Organic Lett 2 3857–3860 Occurrence Handle10.1021/ol000271e
S Carbonnel C Fayet J Gelas Y Troin (2000) ArticleTitleAsymmetric synthesis of C-6 substituted pipecolic acid derivatives. Tetrahedron Lett 41 8293–8296 Occurrence Handle10.1016/S0040-4039(00)01463-5
S Carbonnel Y Troin (2002) ArticleTitleStereoselective synthesis of C-6 substituted pipecolic acid derivatives. Formal synthesis of (+)-indolizidine 167B and (+)-indolizidine 209D. Heterocycles 57 1807–1830
P Celestini B Danieli G Lesma A Sacchetti A Silvani D Passarella A Virdis (2002) ArticleTitletrans-6-Aminocyclohept-3-enols a new designed polyfunctionalized chiral building block for the asymmetric synthesis of 2-substituted-4-hydroxypiperidines. Organic Lett 4 1367–1370 Occurrence Handle10.1021/ol025683x
M Cellier Y Gelas-Mialhe HP Husson B Perrin R Remuson (2000) ArticleTitleEnantioselective synthesis of 5-substituted pipecolic acids using an intramolecular allylsilane-iminium ion cyclization. Tetrahedron: Asymm 11 3913–3919 Occurrence Handle10.1016/S0957-4166(00)00361-X
R Chênevert MP Morin (1999) ArticleTitleChemoenzymatic synthesis of both enantiomers of cis-6-hydroxymethyl- and cis,cis-4-hydroxy-6-(hydroxymethyl)pipecolic acids. J Org Chem 64 3178–3180 Occurrence Handle10.1021/jo9823036 Occurrence Handle11674418
TD Copeland EM Wondrak J Tozser MM Roberts S Oroszlan (1990) ArticleTitleSubstitution of proline with pipecolic acid at the scissile bond converts a peptide substrate of HIV proteinase into a selective inhibitor. Biochem Biophys Res Comm 169 310–314 Occurrence Handle10.1016/0006-291X(90)91469-9 Occurrence Handle2190554
EJ Corey MC Noe F Xu (1998) ArticleTitleHighly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst. Tetrahedron Lett 39 5347–5350 Occurrence Handle10.1016/S0040-4039(98)01067-3
F Couty (1999) ArticleTitleAsymmetric syntheses of pipecolic acid and derivatives. Amino Acids 16 297–320 Occurrence Handle10.1007/BF01388174 Occurrence Handle10399018
CE Davies TD Heightman SA Hermitage MG Moloney (1996) ArticleTitleConvenient preparations of racemic and enantiopure methyl 6-oxopipecolate. Synthetic Commun 26 687–696
Davis FA, Fang T, Chao B, Burns DM (2000) Asymmetric synthesis of the four stereoisomers of 4-hydroxypipecolic acid. Synthesis: 2106–2112
FA Davis H Zhang SH Lee (2001) ArticleTitleMasked oxo sulfinimines (N-sulfinyl imines) in the asymmetric synthesis of proline and pipecolic acid derivatives. Organic Lett 3 759–762 Occurrence Handle10.1021/ol015520t
C Di Nardo O Varela (1999) ArticleTitleEnantioselective synthesis of (2R,4S)- and (2S,4R)-4-hydroxypipecolic acid from D-glucoheptono-1,4-lactone. J Org Chem 64 6119–6125 Occurrence Handle10.1021/jo990445+
FX Felpin J Lebreton (2004) ArticleTitleSynthesis of 2,6-dialkyl-1,2,5,6-tetrahydropyridines and their application in total synthesis. Curr Org Synt 1 83–109 Occurrence Handle10.2174/1570179043485420
GA Flynn EL Giroux RC Dage (1987) ArticleTitleAn acyl-iminium ion cyclization route to a novel conformationally restricted dipeptide mimic: applications to angiotensin-converting enzyme inhibition. J Am Chem Soc 109 7914–7915 Occurrence Handle10.1021/ja00259a068
T Fujita M Fujita T Kodama T Hada K Higashino (2003) ArticleTitleDetermination of D- and L-pipecolic acid in food samples including processed foods. Ann Nutri Metab 47 165–169 Occurrence Handle10.1159/000070040
X Ginesta MA Pericás A Riera (2002) ArticleTitleStraightforward entry to the pipecolic acid nucleus. Enantioselective synthesis of baikiain. Tetrahedron Lett 43 779–782 Occurrence Handle10.1016/S0040-4039(01)02271-7
Goldspink NJ, Simpkins NS, Beckmann M (1999) Highly enantioselective synthesis of substituted piperidines using the chiral lithium amide base approach. Synlett: 1292–1294
AS Golubev H Schedel G Radics J Sieler K Burger (2001) ArticleTitleStereoselective syntheses of 4-fluoro- and 4,4-difluoropipecolic acids. Tetrahedron Lett 42 7941–7944 Occurrence Handle10.1016/S0040-4039(01)01660-4
R Grandel U Kazmaier F Rominger (1998) ArticleTitleShort syntheses of polyhydroxylated α-alkylated amino acids. J Org Chem 63 4524–4528 Occurrence Handle10.1021/jo980205e
TJ Greshock RL Funk (2002) ArticleTitle6-Bromomethyl-4H-1,3-dioxin: a versatile bromomethyl vinyl ketone equivalent for heterocycle and carbocycle construction. J Am Chem Soc 124 754–755 Occurrence Handle10.1021/ja0123554 Occurrence Handle11817942
G Guillena C Nájera (2000) ArticleTitle1,5-Dimethyl-4-phenylimidazolidin-2-one-derived iminic glycinimides: useful new reagents for practical asymmetric synthesis of α-amino acids. J Org Chem 65 7310–7322 Occurrence Handle10.1021/jo000321t Occurrence Handle11076588
MC Gutierrez BA Delgado-Coello (1989) ArticleTitleInfluence of pipecolic acid on the release and uptake of [3H]GABA from brain slices of mouse cerebral cortex. Neurochem Res 14 405–408 Occurrence Handle10.1007/BF00964852 Occurrence Handle2747832
M Haddad M Larchevêque (1999) ArticleTitleA new route to (2S,4R)- and (2R,4S)-4-hydroxypipecolic acid. Tetrahedron: Asymm 10 4231–4237 Occurrence Handle10.1016/S0957-4166(99)00458-9
A Hercouet B Bessières M Le Corre L Toupet (1996) ArticleTitleSynthesis of optically active 2,3-methanopipecolic acid. Tetrahedron Lett 37 4529–4532 Occurrence Handle10.1016/0040-4039(96)00875-1
C Herdeis E Heller (1997) ArticleTitleSynthesis of (2S,4S,5S)-5-hydroxy-4-methylpipecolic acid via amide methylenation of 5-hydroxy-4-methyl-2-piperidinone with dimethyltitanocene. Tetrahedron: Asymm 8 1115–1121 Occurrence Handle10.1016/S0957-4166(97)00091-8
B Ho TM Zabriskie (1998) ArticleTitleEpoxide derivatives of pipecolic acid and proline are inhibitors of pipecolate oxidase. Bioorg Med Chem Lett 8 739–744 Occurrence Handle10.1016/S0960-894X(98)00106-1 Occurrence Handle9871533
M Horikawa J Bush-Petersen EJ Corey (1999) ArticleTitleEnantioselective synthesis of β-hydroxy-α-amino acid esters by aldol coupling using a chiral quaternary ammonium salt as catalyst. Tetrahedron Lett 40 3843–3846 Occurrence Handle10.1016/S0040-4039(99)00636-X
RE Ireland JL Gleason LD Gegnas TKA Highsmith (1996) ArticleTitleTotal synthesis of FK-506. J Org Chem 61 6856–6872 Occurrence Handle10.1021/jo951646q Occurrence Handle11667580
H Ishitani S Komiyama Y Hasegawa S Kobayashi (2000) ArticleTitleCatalytic asymmetric Strecker synthesis. Preparation of enantiomerically pure α-amino acid derivatives from aldimines and tributyltin cyanide or achiral aldehydes, amines and hydrogen cyanide using a chiral zirconium catalyst. J Am Chem Soc 122 762–766 Occurrence Handle10.1021/ja9935207
Jackson RFW, Turner D, Block MH (1997) Stereospecific allylation of a serine-derived zinc/copper reagent. Synthesis of substituted pipecolic acid derivatives. Synlett 789–790
Jourdant A, Zhu J (2000) An efficient stereoselective and stereodivergent synthesis of (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids. Tetrahedron Lett 41: 7033–7036
T Kanayama K Yoshida H Miyabe T Kimachi Y Takemoto (2003) ArticleTitleSynthesis of β-substituted α-amino acids with use of iridium-catalyzed asymmetric allylic substitution. J Org Chem 68 6197–6201 Occurrence Handle10.1021/jo034638f Occurrence Handle12895050
R Kikumoto Y Tamao T Tezuka S Tonomura H Hara K Ninomiya A Hijikata S Okamoto (1984) ArticleTitleSelective inhibition of thrombin by (2R,4R)-4-methyl-1-[N2-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)-sulfonyl]-L-arginyl]-2-piperidinecarboxylic acid. Biochemistry 23 85–90 Occurrence Handle10.1021/bi00296a014 Occurrence Handle6691968
SD Koulocheri P Magiatis AL Skaltsounis SA Haroutounian (2002) ArticleTitleAsymmetric synthesis of (2R,3S)-3-hydroxypipecolic acid δ-lactam derivatives. Tetrahedron 58 6665–6671 Occurrence Handle10.1016/S0040-4020(02)00674-9
A Kulesza A Mieczkowski J Jurczak (2002) ArticleTitleDiastereoselective allylation of chiral imines and a stereocontrolled route to 4-hydroxy-N-tosylpipecolic acid derivatives. Tetrahedron: Asymm 13 2061–2069 Occurrence Handle10.1016/S0957-4166(02)00542-6
Kummeter M, Kazmaier U (2003) Synthesis of monocyclic and bicyclic imino sugars. Eur J Org Chem: 3330–3334
D Lamarre G Croteau E Wardrop L Bourgon D Thibeault C Clouette M Vaillancourt E Cohen C Pargellis C Yoakim PC Anderson (1997) ArticleTitleAntiviral properties of Palinavir a potent inhibitor of the human immunodeficiency virus type 1 protease D. Antimicrob Agents Chemother 41 965–971 Occurrence Handle9145853
JF Lau TK Hansen JP Kilburn K Frydenvang DD Holsworth Y Ge RT Uyeda LM Judge HS Andersen (2002) ArticleTitleA convenient large scale chiral synthesis of protected 2-substituted 4-oxo piperidine derivatives. Tetrahedron 58 7339–7344 Occurrence Handle10.1016/S0040-4020(02)00682-8
Lee BW, Jeong IY, Yang MS, Choi MS, Park KH (2000) A short and efficient synthesis of 2R,3R,4R-3,4-dihydroxyproline, 1,4-dideoxy-1,4-imino-L-xylitol,2R,3R,4R,5S-3,4,5-trihydroxypipecolic acid, and 1,5-dideoxy-1,5-imino-L-iditol. Synthesis: 1305–1309
MA Letavic MZ Axt JT Barberia TJ Carty DE Danley KF Geoghegan NS Halim LR Hoth AV Kamath ER Laird LL Lopresti-Morrow KF McClure PG Mitchell V Natarajan MC Noe J Pandit L Reeves GK Schulte SL Snow FJ Sweeney DH Tan CH Yu (2002) ArticleTitleSynthesis and biological activity of selective pipecolic acid-based TNF-α converting enzyme (TACE) inhibitors. Bioorg Med Chem Lett 12 1387–1390 Occurrence Handle10.1016/S0960-894X(02)00183-X Occurrence Handle11992783
DG Liu Y Gao X Wang JA Kelley TR Burke SuffixJr (2002a) ArticleTitleEnantioselective synthesis of Nα-Fmoc protected (2S,3R)-3-phenylpipecolic acid. A constrained phenylalanine analogue suitably protected for solid-phase peptide synthesis. J Org Chem 67 1448–1452 Occurrence Handle10.1021/jo010124+
DG Liu XZ Wang Y Gao B Li D Yang TR Burke SuffixJr (2002b) ArticleTitleSynthesis of N-Fmoc 3-(4-(di-(tert-butyl)phosphonomethyl)-penyl)pipecolic acid as a conformationaly constrained phosphotyrosyl mimetic suitably protected for peptide synthesis. Tetrahedron 58 10423–10428 Occurrence Handle10.1016/S0040-4020(02)01421-7
Machetti F, Cordero FM, De Sarlo F, Papini AM, Alcaro MC, Brandi A (2004) Synthesis of free and Nα-Fmoc-/Nγ-Boc-protected (2S,4S)- and (2S,4R)-4-aminopipecolic acids. Eur J Org Chem 2928–2935
W Maison G Adiwidjaja (2002) ArticleTitleA short stereoselective synthesis of disubstituted cyclic amino acids. Tetrahedron Lett 43 5957–5960 Occurrence Handle10.1016/S0040-4039(02)01267-4
J Marin C Didierjean A Aubry JR Casimir JP Briand G Guichard (2004) ArticleTitleSynthesis of enantiopure 4-hydroxypipecolate and 4-hydroxylysine derivatives from a common 4,6-dioxopiperidinecarboxylate precursor. J Org Chem 69 130–141 Occurrence Handle10.1021/jo0353886 Occurrence Handle14703388
J Martin MC Lasne JC Plaquevent L Duhamel (1997) ArticleTitleEnantioselective protonation of amide enolates derived from piperidine-2-carboxylic acid. Tetrahedron Lett 38 7181–7182 Occurrence Handle10.1016/S0040-4039(97)01705-X
H Moriyama T Tsukida Y Inoue H Kondo K Yoshino SI Nishimura (2003) ArticleTitleStructure-activity relationships of azasugar-based MMP/ADAM inhibitors. Bioorg Med Chem Lett 13 2737–2740 Occurrence Handle10.1016/S0960-894X(03)00530-4 Occurrence Handle12873504
S Nazabadioko RJ Pérez R Brieva V Gotor (1998) ArticleTitleChemoenzymatic synthesis of (S)-2-cyanopiperidine a key intermediate in the route to (S)-pipecolic acid and 2-substituted piperidine alkaloids. Tetrahedron: Asymm 9 1597–1604 Occurrence Handle10.1016/S0957-4166(98)00140-2
PL Ornstein MB Arnold WHW Lunn LJ Heinz JD Leander D Lodge DD Schoepp (1998) ArticleTitleHeteroatom-substitution as a strategy for increasing the potency of competitive NMDA antagonists. Bioorg Med Chem Lett 8 389–394 Occurrence Handle10.1016/S0960-894X(98)00038-9 Occurrence Handle9871691
B Pal S Ikeda H Kominami Y Kera B Ohtani (2003) ArticleTitlePhotocatalytic redox-combined synthesis of L-pipecolinic acid from L-lysine by suspended titania particles: effect of noble metal loading on the selectivity and optical purity of the product. J Catalysis 217 152–159
Partogyan-Halim K, Besson L, Aitken DJ, Husson HP (2003) Asymmetric synthesis of (S)-4-oxopipecolic acid by a 3 + 3 atom-unit assembly strategy. Eur J Org Chem: 268–273
LMA Rogers J Rouden L Lecomte MC Lasne (2003) ArticleTitleEnantioselective decarboxylation-reprotonation of an α-amino malonate derivative as a route to optically enriched cyclic α-amino acid. Tetrahedron Lett 44 3047–3050 Occurrence Handle10.1016/S0040-4039(03)00557-4
GHP Roos KA Dastlik (2000) ArticleTitleHighly diastereoselective alkylation of the Dellaria oxazinone template with bifunctional electrophiles. Synthetic Commun 33 2197–2208 Occurrence Handle10.1081/SCC-120021497
FPJT Rutjes HE Schoemaker (1997) ArticleTitleRuthenium-catalyzed ring closing olefin metathesis of non-natural α-amino acids. Tetrahedron Lett 38 677–680 Occurrence Handle10.1016/S0040-4039(96)02390-8
Rutjes FPJT, Veerman JJN, Meester WJN, Hiemstra H, Schoemaker HE (1999) Synthesis of enantiopure functionalized pipecolic acids via amino acid derived N-acyliminium ions. Eur J Org Chem: 1127–1135
M Sabat CR Johnson (2001) ArticleTitleSynthesis of (2R,4R)- and (2S,4S)-4-hydroxypipecolic acid derivatives and (2S,4S)-(−)-SS20846A. Tetrahedron Lett 42 1209–1212 Occurrence Handle10.1016/S0040-4039(00)02124-9
NU Sata R Kuwahara Y Murata (2002) ArticleTitleSynthesis of all isomers of pulcherrimine a bitter principle in the sea urchin ovary. Tetrahedron Lett 43 115–118 Occurrence Handle10.1016/S0040-4039(01)02095-0
JD Scott TN Tippie RM Williams (1998) ArticleTitleSynthetic studies on Tetrazomine: stereochemical assignment of the β-hydroxypipecolic acid. Tetrahedron Lett 39 3659–3662 Occurrence Handle10.1016/S0040-4039(98)00642-X
JD Scott RM Williams (2002) ArticleTitleTotal synthesis of (−)-Tetrazomine. Determination of the stereochemistry of Tetrazomine and the synthesis and biological activity of Tetrazomine analogues. J Am Chem Soc 124 2951–2956 Occurrence Handle10.1021/ja0174027 Occurrence Handle11902886
ZD Shi BH Yang YL Wu YJ Pan YY Ji M Yeh (2002) ArticleTitleFirst example of an antibody-catalyzed aza-Diels-Alder reaction. Bioorg Med Chem Lett 12 2321–2324 Occurrence Handle10.1016/S0960-894X(02)00402-X Occurrence Handle12161125
JP Shilvock RJ Nash JD Lloyd AL Winters N Asano GWJ Fleet (1998) ArticleTitleIntermediates for incorporation of tetrahydroxypipecolic acid analogues of α- and β-D-mannopyranose into combinatorial libraries: unexpected nanomolar-range hexosaminidase inhibitors. Synthesis of α- and β-homomannojirimycin. Tetrahedron: Asymm 9 3505–3516 Occurrence Handle10.1016/S0957-4166(98)00365-6
JP Shilvock JR Wheatley RJ Nash AA Watson RC Griffiths TD Butters M Müller DJ Watkin DA Winkler GW Fleet (1999) ArticleTitleSynthesis of homorhamnojirimycins and related trihydroxypipecolic acid derivatives via divergent bicyclic amino lactone intermediates: inhibition of naringinase (L-rhamnosidase) and dTDP-rhamnose biosynthesis. J Chem Soc, Perkin Trans 1 2735–2745
PS Shirude VA Kumar KN Ganesh (2004) ArticleTitleChimeric peptide nucleic acids incorporating (2S,5R)-aminoethyl pipecolyl units: synthesis and DNA binding studies. Tetrahedron Lett 45 3085–3088 Occurrence Handle10.1016/j.tetlet.2004.02.099
AB Smith SuffixIII SM Condon JA McCauley JL Leazer SuffixJr JW Leahy RE Maleczka (1997) ArticleTitleA unified total synthesis of the immunomodulators (−)-rapamycin and (−)-27-demethoxyrapamycin: assembly of the common C(1–20) perimeter and final elaboration. J Am Chem Soc 119 962–973 Occurrence Handle10.1021/ja963067o
AJ Souers JA Ellman (2000) ArticleTitleAsymmetric synthesis of a C-3 substituted pipecolic acid. J Org Chem 65 1222–1224 Occurrence Handle10.1021/jo991293l Occurrence Handle10814077
ME Swarbrick F Gosselin WD Lubell (1999) ArticleTitleAlkyl substituent effects on pipecolyl amide isomer equilibrium: efficient methodology for synthesizing enantiopure 6-alkylpipecolic acids and conformational analysis of their N-acetyl N′-methylamides. J Org Chem 64 1993–2002 Occurrence Handle10.1021/jo982181h Occurrence Handle11674294
H Takahata M Shimizu (2003) ArticleTitleAsymmetric synthesis of all stereoisomers of 6-methylpipecolic acids. Amino Acids 24 267–272 Occurrence Handle10.1007/s00726-002-0411-8 Occurrence Handle12707808
Teoh E, Campi EM, Jackson WR, Robinson AJ (2002) A highly enantioselective synthesis of cyclic α-amino acids involving a one-pot single catalyst tandem hydrogenation-hydroformylation sequence. Chem Commun: 978–979
E Teoh EM Campi WR Jackson AJ Robinson (2003) ArticleTitleOne-pot tandem hydrogenation-hydroformylation synthesis of cyclic α-amino acids. New J Chem 27 387–394 Occurrence Handle10.1039/b209087m
Tjen KCMF, Kinderman SS, Schoemaker HE, Hiemstra H, Rutjes FPJT (2000) A ring-closing metathesis-mediated route to novel enantio pure conformationally restricted cyclic amino acids. Chem Commun: 699–700
H Vanderhaeghe G Janssen F Compernolle (1971) ArticleTitleThe structure of minor components of virginiamycin S. Tetrahedron Lett 12 2687–2688 Occurrence Handle10.1016/S0040-4039(01)96952-7
Varray S, Lazaro R, Martinez J, Lamaty F (2002) A new soluble polymer-supported sulfonyl linker – Application to the synthesis of cyclic α-amino acids. Eur J Org Chem: 2308–2316
PM Weintraub JS Sabol JM Kane DR Borcherding (2003) ArticleTitleRecent advances in the synthesis of piperidones and piperidines. Tetrahedron 59 2953–2989 Occurrence Handle10.1016/S0040-4020(03)00295-3
TJ Wilkinson NW Stehle P Beak (2000) ArticleTitleEnantioselective syntheses of 2-alkyl- and 2,6-dialkylpiperidine alkaloids: preparations of the hydrochlorides of (−)-coniine(−)-solenopsin A, and (−)-dihydropinidine. Organic Lett 2 155–158 Occurrence Handle10.1021/ol9912534
CB Xue X He J Roderick RL Corbett CP Decicco (2002) ArticleTitleAsymmetric synthesis of trans-2,3-piperidine dicarboxylic acid and trans-3,4-piperidine dicarboxylic acid derivatives. J Org Chem 67 865–870 Occurrence Handle10.1021/jo016086b Occurrence Handle11856030
RM Zacharius JF Thompson FC Steward (1952) ArticleTitleThe detection, isolation and identification of (−)-pipecolic acid as a constituent of plants. J Am Chem Soc 74 2949 Occurrence Handle10.1021/ja01131a529
A Zaparucha M Danjoux A Chiaroni J Royer HP Husson (1999) ArticleTitleAsymmetric synthesis of 3-alkyl pipecolic acids. Tetrahedron Lett 40 3699–3700 Occurrence Handle10.1016/S0040-4039(99)00591-2
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kadouri-Puchot, C., Comesse, S. Recent advances in asymmetric synthesis of pipecolic acid and derivatives. Amino Acids 29, 101–130 (2005). https://doi.org/10.1007/s00726-005-0193-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00726-005-0193-x