Asymmetric Palladium-catalyzed Carboamination Reactions for the Synthesis of Enantiomerically Enriched 2-(arylmethyl)- and 2-(alkenylmethyl)pyrrolidines

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2010 Aug 20

PMID 20718417

Citations 42

Authors

Duy N Mai

John P Wolfe

Affiliations

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Abstract

The enantioselective synthesis of 2-(arylmethyl)- and 2-(alkenylmethyl)pyrrolidine derivatives via Pd-catalyzed alkene carboamination reactions is described. These transformations generate enantiomerically enriched products with up to 94% ee from readily available alkenyl or aryl bromides and N-boc-pent-4-enylamines. The application of this method to a concise asymmetric synthesis of (-)-tylophorine is also discussed.

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