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Communication | Special issue | Vol 35, No. 1, 1993, pp.73-76
Published online, 1st January, 1970
DOI: 10.3987/COM-92-S27
The Lewis Acid-catalyzed Intramolecular Asymmetric Hetero Diels-Alder Reaction of Chiral α'-Sulfinyl-α,β-unsaturated Ketone. A Chiral Diene Bearing an Optically Active Sulfinylmethyl Group

Kunio Hiroi,* Masayuki Umemura, and Yoko Tomikawa

*Department of Synthetic Organic Chemistry, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Abstract

This paper presents an asymmetric Diels-Alder reaction with a diene bearing a chiral sulfinyl group. The Lewis acid-catalyzed intramolecular asymmetric hetero Diels-Alder reaction of a chiral α’-sulfinyl-α,β-unsaturated ketone derived from ˙3-methylcitronellal produced optically active 4a,5,6,7,8,8a-hexahydro-1H-2-benzopyran derivatives. On the basis of the stereochemical results obtained, a plausible mechanism for the asymmetric induction is presented.