HIGHLY STEREOSELECTIVE HYDROCYANATION OF OPTICALLY PURE ALPHA-SULFINYLALDEHYDES

Authors
GARCIA MMC RUANO JLG CASTRO AMM RAMOS JHR FERNANDEZ I
Citation
Mmc. Garcia et al., HIGHLY STEREOSELECTIVE HYDROCYANATION OF OPTICALLY PURE ALPHA-SULFINYLALDEHYDES, Tetrahedron : asymmetry, 9(5), 1998, pp. 859-864
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
5
Year of publication
1998
Pages
859 - 864
Database
ISI
SICI code
0957-4166(1998)9:5<859:HSHOOP>2.0.ZU;2-U
Abstract
Diastereoselective hydrocyanation of enantiomerically pure 2-p-tolyl-s ulfinylacetaldehyde and 2-p-tolylsulfinylpropanal with Et2AlCN catalyz ed by ZnBr2 is described. The sulfur configuration controls the stereo chemical course of the reaction. Hydrolysis of the resulting cyanohydr ins and further desulfurization yielded the corresponding alpha-hydrox yamides in high ees (90%). (C) 1998 Elsevier Science Ltd. All rights r eserved.