Issue 8, 1996

A highly asymmetric, Lewis acid-catalysed Diels–Alder reaction using optically active 2-(3-tolyl p-sulfinyl)furyl α,β-unsaturated ketones as a dienophile

Abstract

The Diels–Alder reaction of chiral 2-(3-tolyl p-sulfinyl)furyl α,β-unsaturated ketones 3 and 4 with cyclopentadiene in the presence of a Lewis acid proceeds smoothly to give the corresponding endo adducts 5a and 6a, respectively, in excellent yield with high diastereoselectivity.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1996, 759-762

A highly asymmetric, Lewis acid-catalysed Diels–Alder reaction using optically active 2-(3-tolyl p-sulfinyl)furyl α,β-unsaturated ketones as a dienophile

Y. Arai, T. Masuda, Y. Masaki and M. Shiro, J. Chem. Soc., Perkin Trans. 1, 1996, 759 DOI: 10.1039/P19960000759

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