Asymmetric aza-Michael addition: synthesis of (-)-allosedridine and (-)-2-epi-ethylnorlobelol

Li Ju Chen, Duen Ren Hou

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

The combination of cross-metathesis and aza-Michael addition is an efficient method for generating piperidine alkaloids. Allosedridine and 2-epi-ethylnorlobelol were synthesized in six steps with ca. 25% overall yield. The aza-Michael addition is reversible for phenyl and alkyl ketones; however, the epimerization is not observed for the corresponding ester and amide.

Original languageEnglish
Pages (from-to)715-720
Number of pages6
JournalTetrahedron: Asymmetry
Volume19
Issue number6
DOIs
StatePublished - 3 Apr 2008

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