Pd. Bailey et al., STEREOSPECIFIC REDUCTION OF A BETA-KETO-NITRILE - FORMATION OF A SINGLE INDOLIC BETA-HYDROXY-NITRILE FROM A MIXTURE OF TAUTOMERS AND DIASTEREOISOMERS, Tetrahedron letters, 35(21), 1994, pp. 3585-3586
The beta-keto-nitrile 2, which is an advanced intermediate for the syn
thesis of several indole alkaloids, is composed of a mixture of enol/k
eto tautomers, and of diastereoisomers; nevertheless, reduction with s
odium borohydride yields essentially a single diastereoisomer 3.