STEREOSPECIFIC REDUCTION OF A BETA-KETO-NITRILE - FORMATION OF A SINGLE INDOLIC BETA-HYDROXY-NITRILE FROM A MIXTURE OF TAUTOMERS AND DIASTEREOISOMERS

Authors
BAILEY PD HOLLINSHEAD SP MOORE MH MORGAN KM SMITHE DI VERNON JM
Citation
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
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
21
Year of publication
1994
Pages
3585 - 3586
Database
ISI
SICI code
0040-4039(1994)35:21<3585:SROAB->2.0.ZU;2-6
Abstract
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.