<Review>Asymmetric Diels-Alder Reactions Using Chiral α, β-Unsaturated Sulfoxides as Efficient Dienophiles

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概要

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• This review reports on our recent studies on asymmetric Diels-Alder reactions of chiral α, β-unsaturated sulfoxides. For the preparation of these sulfoxides as Diels-Alder dienophiles, the Andersen method as well as a novel route by diastereoselective oxidation of 2-exo-hydroxy-10-bornyl vinyl sulfides with 3-chloroperoxybenzoic acid is presented. The latter methodology has been successfully applied to synthesis of two types of novel sulfoxides bearing labile fuctionality, I.e., α-sulfinylmaleate and α -sulfinylmaleimide derivatives. These sulfinyl dienophiles effect Diels-Alder reactions with a high degree of diastereoselectivity. Especially, the chiral α-sulfinylmaleimides readily react with Diels-Alder dienes of rather low reactivity, to give the corresponding cycloadducts under conventional conditions. Also described are applications of these asymmetric Diels-Alder reactions to natural product synthesis.

• 岐阜薬科大学の論文
• 1995-06-30

著者

• Arai Yoshitsugu

  岐阜薬科大学

関連論文

• Asymmetric Diels-Alder Reactions Using Chiral α, β-Unsaturated Sulfoxides as Efficient Dienophiles

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