A HIGHLY ASYMMETRIC, LEWIS ACID-CATALYZED DIELS-ALDER REACTION USING OPTICALLY-ACTIVE 2-(3-TOLYL-P-SULFINYL)FURYL ALPHA,BETA-UNSATURATED KETONES AS A DIENOPHILE

Authors
ARAI Y MASUDA T MASAKI Y SHIRO M
Citation
Y. Arai et al., A HIGHLY ASYMMETRIC, LEWIS ACID-CATALYZED DIELS-ALDER REACTION USING OPTICALLY-ACTIVE 2-(3-TOLYL-P-SULFINYL)FURYL ALPHA,BETA-UNSATURATED KETONES AS A DIENOPHILE, Journal of the Chemical Society. Perkin transactions. I, (8), 1996, pp. 759-762
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
8
Year of publication
1996
Pages
759 - 762
Database
ISI
SICI code
0300-922X(1996):8<759:AHALAD>2.0.ZU;2-7
Abstract
The Diels-Alder reaction of chiral 2-(3-tolyl-p-sulfinyl)furyl alpha,b eta-unsaturated ketones 3 and 4 with cyclopentadiene in the presence o f a Lewis acid proceeds smoothly to give the corresponding endo adduct s 5a and 6a, respectively, in excellent yield with high diastereoselec tivity.