Tetrahedron: Asymmetry

Chemoenzymatic synthesis of (S)-2-cyanopiperidine, a key intermediate in the route to (S)-pipecolic acid and 2-substituted piperidine alkaloids

S Nazabadioko, RJ Pérez, R Brieva, V Gotor

Index: Nazabadioko, Serge; Perez, Ramon J.; Brieva, Rosario; Gotor, Vicente Tetrahedron Asymmetry, 1998 , vol. 9, # 9 p. 1597 - 1604

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Citation Number: 57

Abstract

The preparation of (S)-2-cyanopiperidine 4 provides a new access to 2-substituted piperidines. This synthesis is based on an enantioselective (R)-oxynitrilase-catalyzed reaction for the preparation of (R)-(+)-6-bromo-2-hydroxyhexanenitrile 1 and the subsequent cyclization of this compound to yield the piperidine ring. The utilization of 4 as the starting material for the synthesis of (S)-2-aminomethylpiperidine 6,(R)-(−)-coniine 10 and (S)-(−)- ...