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Chiral pyrrolidine diamines as efficient ligands in asymmetric synthesis

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Organic Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 127))

Abstract

Complex biologically active substances possessing an array of chiral centers within the same molecule continue to be challenging synthetic targets in organic chemistry. The synthesis of such complex compounds in optically active form has led to the concept of “the asymmetric reaction”, a potentially direct and effective method for the construction of chiral framework. Herein, a historical review of new and useful highly selective asymmetric reactions developed in our laboratory, employing chiral diamines and amino alcohols derived easily from (S)-proline, is described. The high selectivity observed in these reactions is postulated to result from efficient non-covalent bonded interactions between organometallic reagent and chiral auxiliary, offering a conceptually new dimension to asymmetric synthesis. Application to the successful synthesis of several natural products is also illustrated.

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Abbreviations

Z:

benzyloxycarbonyl

DCC:

dicyclohexylcarbodiimide

LiAlH4 :

lithium aluminium hydride

BOC:

tert-butoxycarbonyl

HBr:

hydrogen bromide

AcOH:

acetic acid

e.e.:

enantiomeric excess

DIBAL-H:

diisobutylaluminium hydride

CuI:

cuprous iodide

CH2Cl2 :

dichloromethane

TMEDA:

N,N,N′,N′-tetramethylethylenediamine

LiAlH(OBut)3 :

lithium tri-tert-butoxyaluminium hydride

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, The University of Tokyo, Hongo, Bunkyo-ku, 113, Tokyo, Japan

    Teruaki Mukaiyama & Masatoshi Asami

Authors
  1. Teruaki Mukaiyama
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  2. Masatoshi Asami
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© 1985 Springer-Verlag

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Mukaiyama, T., Asami, M. (1985). Chiral pyrrolidine diamines as efficient ligands in asymmetric synthesis. In: Organic Chemistry. Topics in Current Chemistry, vol 127. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0049440

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  • DOI: https://doi.org/10.1007/BFb0049440

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