ACYCLIC STEREOCONTROL IN THE ADDITION OF TRIMETHYLSILYL CYANIDE TO N-SUBSTITUTED IMINES OF (2S)-LACTIC ALDEHYDE

Authors
CAINELLI G GIACOMINI D TRERE A GALLETTI P
Citation
G. Cainelli et al., ACYCLIC STEREOCONTROL IN THE ADDITION OF TRIMETHYLSILYL CYANIDE TO N-SUBSTITUTED IMINES OF (2S)-LACTIC ALDEHYDE, Tetrahedron : asymmetry, 6(7), 1995, pp. 1593-1600
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
7
Year of publication
1995
Pages
1593 - 1600
Database
ISI
SICI code
0957-4166(1995)6:7<1593:ASITAO>2.0.ZU;2-5
Abstract
The cyanosilylation of a series of N-substituted lactaldehyde imines i s reported. The trimethylsilylcyanide addition affords optically activ e alpha-amino nitriles. All the imines show a syn diastereofacial sele ctivity that is maintained irrespective to the nature of the Lewis aci d employed and even remains in the noncatalyzed reaction.