REDUCTION OF ALPHA-TRIALKYLSILOXY NITRILES WITH DIISOBUTYLALUMINIUM HYDRIDE (DIBAH) - A FACILE PREPARATION OF ALPHA-TRIALKYLSILOXY ALDEHYDES AND THEIR DERIVATIVES

Authors
HAYASHI M YOSHIGA T NAKATANI K ONO K OGUNI N
Citation
M. Hayashi et al., REDUCTION OF ALPHA-TRIALKYLSILOXY NITRILES WITH DIISOBUTYLALUMINIUM HYDRIDE (DIBAH) - A FACILE PREPARATION OF ALPHA-TRIALKYLSILOXY ALDEHYDES AND THEIR DERIVATIVES, Tetrahedron, 50(9), 1994, pp. 2821-2830
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
9
Year of publication
1994
Pages
2821 - 2830
Database
ISI
SICI code
0040-4020(1994)50:9<2821:ROANWD>2.0.ZU;2-X
Abstract
The stepwise synthesis of alpha-trimethylsiloxy aldehydes and alpha-hy droxy aldehydes could be acheived via the reduction of alpha-trimethyl siloxy nitriles with diisobuytylaluminium hydride (DIBAH) starting fro m a variety of ketones. The facile synthesis of optically active alpha -tert-butyldimethylsiloxy aldehydes was attained by combination of asy mmetric silylcyanation of aldehydes and DIBAH reduction of optically a ctive alpha-siloxy nitriles. Furthermore, in the reduction of some ha- tert-butyldimethylsiloxy-beta,gamma-unsaturated nitriles, migration of the double bond took place to form more stable alpha-siloxy-alpha,bet a-unsaturated aldehydes under some reactions conditions.