Catalytic Asymmetric Cyanohydrin Synthesis

Michael North

doi:10.1055/s-1993-22618

Synlett 1993; 1993(11): 807-820
DOI: 10.1055/s-1993-22618

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Catalytic Asymmetric Cyanohydrin Synthesis

Michael North^*

^*Department of Chemistry, University of Wales, Bangor, Gwynedd LL57 2UW, England

Abstract

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The use of various catalysts in the asymmetric addition of HCN (or an equivalent) to achiral aldehydes and ketones, giving optically active cyanohydrins is discussed. The catalysts include enzymes, chiral polymers, chiral titanium and boron complexes, and cyclic dipeptides. Special emphasis is given to the synthetic and mechanistic aspects of the reactions catalysed by the diketopiperazine cyclo-[(S)-His-(S)-Phe] (4). 1. Introduction 2. Use of Enzymes 3. Use of Polymers 4. Use of Organometallic Reagents 5. Use of Peptides 6. Mechanistic Aspects of the Reaction Catalysed by Cyclo-[(S)-His-(S)-Phe] 7. Miscellaneous 8. Summary

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