KINETIC RESOLUTION IN ASYMMETRIC ANTI ALDOL REACTIONS OF BRANCHED ANDSTRAIGHT-CHAIN RACEMIC 2-PHENYLSULFANYL ALDEHYDES - ASYMMETRIC-SYNTHESIS OF CYCLIC ETHERS AND LACTONES BY PHENYLSULFANYL MIGRATION

Authors
CHIBALE K WARREN S
Citation
K. Chibale et S. Warren, KINETIC RESOLUTION IN ASYMMETRIC ANTI ALDOL REACTIONS OF BRANCHED ANDSTRAIGHT-CHAIN RACEMIC 2-PHENYLSULFANYL ALDEHYDES - ASYMMETRIC-SYNTHESIS OF CYCLIC ETHERS AND LACTONES BY PHENYLSULFANYL MIGRATION, Journal of the Chemical Society. Perkin transactions. I, (16), 1996, pp. 1935-1940
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
16
Year of publication
1996
Pages
1935 - 1940
Database
ISI
SICI code
0300-922X(1996):16<1935:KRIAAA>2.0.ZU;2-U
Abstract
The kinetic resolution of branched and straight chain 2-phenylsulfanyl aldehydes by the Lewis acid-catalysed asymmetric anti aldol reaction followed by reduction to single enantiomers of 1,3-diols and/or acid-c atalysed cyclisation with PhS migration provides a route to enantiomer ically pure cyclic ethers and lactones with full stereochemical contro l.