Asymmetric Diels-Alder Reactions of α'-Benzenesulfonyl-α,β-Unsaturated Ketones with Cyclopentadiene Catalyzed by a Chiral Titanium Reagent

Abstract

Abstract: Asymmetric Diels-Alder reaction of α'-benzenesulfonyl-α,β-unsaturated ketones with cyclopentadiene using a catalytic amount of a chiral titanium reagent was performed. The Diels-Alder adducts were achieved in high yields and high enantioselectivities. The relationship between the substituent on the dienophile and reactivity and also the optical purity of the product were discussed. The absolute configuration of the cycloadducts was determined by an alternative synthetic route of compound 2 also by an asymmetric Diels-Alder reaction of the acyloxazolidinone 4 with cyclopentadiene, and the nucleophilic addition of benzenesulfonylmethyl lithium to the product.

Key words: Benzensulfonyl, Asymmetric catalysis, Diels-Alder reaction

CLC Number:

O642.12

TrendMD:

PEI Wen. Asymmetric Diels-Alder Reactions of α'-Benzenesulfonyl-α,β-Unsaturated Ketones with Cyclopentadiene Catalyzed by a Chiral Titanium Reagent[J]. Chem. J. Chinese Universities, 1998, 19(3): 402.

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Asymmetric Diels-Alder Reactions of α'-Benzenesulfonyl-α,β-Unsaturated Ketones with Cyclopentadiene Catalyzed by a Chiral Titanium Reagent

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