Ein einfacher Zugang zu (R)-α-Hydroxycarbonsäuren und (R)- 1-Amino-2-alkoholen aus (R)-Cyanhydrinen

Thomas Ziegler; Brigitte Hörsch; Franz Effenberger

doi:10.1055/s-1990-26945

Synthesis 1990; 1990(7): 575-578
DOI: 10.1055/s-1990-26945

paper

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Ein einfacher Zugang zu (R)-α-Hydroxycarbonsäuren und (R)- 1-Amino-2-alkoholen aus (R)-Cyanhydrinen

Thomas Ziegler^* , Brigitte Hörsch, Franz Effenberger

^*Institut für Organische Chemie der Universität Stuttgart, Pfaffenwaldring 55, D-7000 Stuttgart 80, Federal Republic of Germany

Abstract

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A Convenient Route to (R)-α-Hydroxy Carboxylic Acids and (2R)-1-Amino-2-alkanols from (R)-Cyanohydrins (R)-Cyanohyrins, prepared in good to excellent yields with high optical purity by enzyme-catalyzed addition of hydrogen cyanide to aldehydes in organic solvents, are hydrolyzed with concentrated hydrochloric acid at ambient temperature, usually in very high yield, without any trace of racemization to give (R)-α-hydroxy carboxylic acids. Likewise, no racemization is observed by direct reduction of the (R)-cyanohydrins with lithium aluminum hydride to give (2R)-1-amino-2-alkanols.

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