Scientific article
English

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

Published inHelvetica chimica acta, vol. 67, no. 5, p. 1397-1401
Publication date1984-08-08
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 99% enantiomeric purity. The sense of induction was reversed on using the enantiomer of 8 as the auxiliary. The structure of 10 was established by X-ray diffraction analysis.

Citation (ISO format)
VON OPPOLZER, Wolfgang, CHAPUIS, Christian, BERNARDINELLI, Gérald Hugues. Camphor-Derived N-Acryloyl and N-Crotonoyl Sultams: Practical Activated Dienophiles in Asymmetric Diels-Alder Reactions. Preliminary Communication. In: Helvetica chimica acta, 1984, vol. 67, n° 5, p. 1397–1401. doi: 10.1002/hlca.19840670527
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Journal ISSN0018-019X
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