Stereoselective synthesis of cis-decalins via Diels–Alder and double Michael addition of substituted Nazarov reagents-Reference-Cited by-同舟云学术

Stereoselective synthesis of cis-decalins via Diels–Alder and double Michael addition of substituted Nazarov reagents

Published:1992-05-01 Issue:5 Volume:70 Page:1406-1426
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Lavallée Jean-François,Spino Claude,Ruel Réjean,Hogan Keith T.,Deslongchamps Pierre

Abstract

The base-catalyzed cycloaddition and double Michael cyclization of substituted Nazarov reagents and of 1-phenylsulfinyl analogs, with 2-carbomethoxy-2-cyclohexen-1-one 1 yielding cis-decalins is reported. The reaction is highly stereoselective affording cis,cis- or cis, trans-decalins. Mechanistic aspects are briefly discussed.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v92-179

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