Abstract
The known enzymes (R)- and (S)-oxynitrilase catalyze the enantioselective addition of hydrocyanic acid to aldehydes to give (R)- and (S)-cyanohydrins. The optical yields can distinctly be improved by the application of organic solvents (i.e. ethyl acetate or diisopropyl ether) instead of a water/ethanol mixture which was used previously in these reactions. For the enzyme (S)-oxynitrilase Sorghum bicolor evolved to be the best source.
The optically active cyanohydrins can be transformed without any racemization by acid catalyzed hydrolysis into α-hydroxy acids and by hydrogenation with lithium/aluminum hydride into 1,2-amino alcohols. Via addition of Grignard reagents to the O-protected cyanohydrins and follow-up hydrogenation, 1,2-amino alcohols are gained with very high diastereoselectivity. By O-sulfonylation of the (R)- and (S)-cyanohydrins optically active α-sulfonyloxy nitriles are obtained. These nitriles react with various nucleophiles by complete inversion of configuration to form various α-substituted carboxylic acid derivatives, α-azido nitriles, α-amino nitriles, α-amino acids, etc.
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© 1992 Springer Science+Business Media Dordrecht
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Effenberger, F.X. (1992). (R)- and (S)-Cyanohydrins - Their Enzymatic Synthesis and Their Reactions. In: Servi, S. (eds) Microbial Reagents in Organic Synthesis. NATO ASI Series, vol 381. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-2444-7_2
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DOI: https://doi.org/10.1007/978-94-011-2444-7_2
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