Abstract
Abstract An overview of our recent studies on asymmetric Diels-Alder reactions of chiral vinyl sulfoxides (= sulfinylethenes) is described. For the preparation of sulfinylethenes as Diels-Alder dienophiles, the Andersen method as well as a novel route by diastereoselective oxidation of exo-2-hydroxy-10-bornyl vinyl sulfides with 3-chloroperoxybenzoic acid (m-CPBA) is presented. The latter methodology has been successfully applied to a facile synthesis of two types of novel sulfoxides, 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, such as furan, to give the corresponding cycloadducts under conventional conditions. Applications of these asymmetric Diels-Alder reactions to natural product synthesis are also described.
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