STUDIES ON CHIRAL ORGANOSULFUR COMPOUNDS .6. THE USE OF A CHIRAL DIENE BEARING AN OPTICALLY-ACTIVE SULFINYLMETHYL GROUP IN THE LEWIS ACID-CATALYZED INTRAMOLECULAR ASYMMETRIC HETERO-DIELS-ALDER REACTION

Authors
HIROI K UMEMURA M TOMIKAWA Y KANEKO M KATO F
Citation
K. Hiroi et al., STUDIES ON CHIRAL ORGANOSULFUR COMPOUNDS .6. THE USE OF A CHIRAL DIENE BEARING AN OPTICALLY-ACTIVE SULFINYLMETHYL GROUP IN THE LEWIS ACID-CATALYZED INTRAMOLECULAR ASYMMETRIC HETERO-DIELS-ALDER REACTION, Chemical and Pharmaceutical Bulletin, 45(5), 1997, pp. 759-764
Citations number
28
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
45
Issue
5
Year of publication
1997
Pages
759 - 764
Database
ISI
SICI code
0009-2363(1997)45:5<759:SOCOC.>2.0.ZU;2-0
Abstract
An asymmetric Diels-Alder reaction,vith a diene bearing a chiral sulfi nyl group is described. The Lewis acid-catalyzed intramolecular asymme tric hetero Diels-Alder reaction of a chiral alpha'-sulfinyl-alpha,bet a-unsaturated ketone derived from 3-methylcitronellal produced optical ly active 4a,5,6,7,8,8a-hexahydro-1H-2-benzopyran derivatives. On the basis of the stereochemical results obtained, a plausible mechanism fo r the asymmetric induction is presented.