Camphor??Derived N??Acryloyl and N??Crotonoyl Sultams: Practical Activated Dienophiles in Asymmetric Diels??alder Reactions. Preliminary Communication

…, C Chapuis, G Bernardinelli

Index: Oppolzer, Wolfgang; Chapuis, Christian; Bernardinelli, Gerald Helvetica Chimica Acta, 1984 , vol. 67, p. 1397 - 1401

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Citation Number: 251

Abstract

Abstract Starting from (+)-camphor-10-sulfonyl chloride (5), the crystalline sultam 8 was easily prepared. Lewis-acid-promoted Diels-Alder additions of the crystalline N-acry-loyl and N-crotonoyl derivatives 9 and 10, respectively, to cyclopentadiene and 1, 3-butadiene at− 130 to− 78 furnished adducts 11, 12 and 17 with high chiral efficiency. Crystallization of the adducts and nondestructive removal of 8 gave either alcohols 13, 14 and 18 ir acid 19 in ...

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