Synthesis of Carbocycles via Intramolecular Conjugate Additions: Another Solution to the Terpenoid Side Chain Stereochemistry Problem

Alyx-Caroline Guevel; David J. Hart

doi:10.1021/jo951531m

Synthesis of Carbocycles via Intramolecular Conjugate Additions: Another Solution to the Terpenoid Side Chain Stereochemistry Problem

J Org Chem. 1996 Jan 26;61(2):465-472. doi: 10.1021/jo951531m.

Authors

Alyx-Caroline Guevel¹, David J. Hart

Affiliation

¹ Department of Chemistry, The Ohio State University, 120 W. 18th Avenue, Columbus, Ohio 43210.

PMID: 11666962
DOI: 10.1021/jo951531m

Abstract

Intramolecular conjugate additions of keto esters 7-11, mediated by pyrrolidine-acetic acid, provide perhydroindans or bicyclo[6.3.0]undecanes with high levels of diastereoselectivity at the acyclic stereogenic center. Levels of acyclic diastereoselection depend on starting unsaturated ester olefin geometry.