HIGHLY DIASTEREOSELECTIVE HYDROCYANATION OF ALPHA-SULFINYL CYCLOALKANONES

Authors
ESCRIBANO A RUANO JLG CASTRO AMM RODRIGUEZ JH
Citation
A. Escribano et al., HIGHLY DIASTEREOSELECTIVE HYDROCYANATION OF ALPHA-SULFINYL CYCLOALKANONES, Tetrahedron, 50(25), 1994, pp. 7567-7578
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
25
Year of publication
1994
Pages
7567 - 7578
Database
ISI
SICI code
0040-4020(1994)50:25<7567:HDHOAC>2.0.ZU;2-E
Abstract
Hydrocyanation of cyclic alpha-sulfinyl ketones under different condit ions has been studied. The obtained results show that compounds derive d from cyclohexanone react with Et(2)AlCN yielding only sulfinyl cyano hydrins exhibiting different configurations at sulfur and at hydroxyli c carbon. The stereoselectivity is slightly lower but also very high s tarting from alpha-sulfinyl cyclopentanones. The influence of Lewis ac ids as well as the stereochemical course of these reactions have also been discussed.