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

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.