Chemically Catalyzed Asymmetric Cyanohydrin Syntheses

• Published in: Angewandte Chemie International Edition Vol. 43; no. 21; pp. 2752 - 2778
• Main Authors: Brunel, Jean-Michel, Holmes, Ian P.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 17-05-2004; WILEY‐VCH Verlag
• Subjects: asymmetric catalysis; cyanation; cyanohydrins; synthetic methods
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.200300604

Over the past two decades, significant advances have been made towards developing chemically catalyzed asymmetric cyanohydrin syntheses. Preparations that were classically highly substrate specific, often using stoichiometric quantities of reagents, have been revolutionized by a new generation of catalysts. Methods currently available rival, and in many cases surpass, enzymatic procedures in terms of synthetic utility, generic applicability, and enantioselectivity. Such protocols are increasingly finding application in the syntheses of both biologically active natural products and therapeutically important synthetic compounds.
Versatile synthetic intermediates: Chiral cyanohydrins (see formula) can be readily converted into a number of key functional groups with control of absolute stereochemistry. Advances in chemically catalyzed asymmetric cyanation reactions of aldehydes and ketones to form cyanohydrins are described and compared.