Abstract
A flexible asymmetric approach to 2,5-disubstituted cis-decahydroquinolines (DHQs) ring system from glutaraldehyde and methyl (E)-5-nitropent-4-enoate is reported. The enantioselective organocatalytic domino Michael/Henry reaction, subsequent one-pot, four-step transformation involving desulfurization, concomitant nitro and alkene reduction and cyclization, and the one-pot amide reductive alkylation method are the key steps responsible for the stereoselective syntheses of 2,5-di-epi-cis-195 A, N-Bn-5-epi-cis-275 B’ and N-Bn-cis-249D.
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