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, 11 (15), 3398-401

Intramolecular Pyridine Activation-Dearomatization Reaction: Highly Stereoselective Synthesis of Polysubstituted Indolizidines and Quinolizidines

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Intramolecular Pyridine Activation-Dearomatization Reaction: Highly Stereoselective Synthesis of Polysubstituted Indolizidines and Quinolizidines

Guillaume Barbe et al. Org Lett.

Abstract

An unprecedented intramolecular pyridine activation-asymmetric dearomatization reaction is described. This process produces 5-substituted indolizidines and 6-substituted quinolizidines in excellent yields and in a highly regio- and diastereoselective fashion. Formal syntheses of trans-indolizidine alkaloids are presented along with some preliminary results in the formation of C-5 quaternary centers.

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