Reaction of α-(N-Carbamoyl)alkylcuprates with Enantioenriched Propargyl Electrophiles:  Synthesis of Enantioenriched 3-Pyrrolines

R. Karl Dieter,* Ningyi Chen, and Vinayak K. Gore
Howard L. Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina 29634-0973
J. Org. Chem., 2006, 71 (23), pp 8755–8760
DOI: 10.1021/jo061442h
Publication Date (Web): October 13, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, dieterr@clemson.edu

Abstract

Abstract Image

Enantioenriched propargyl mesylates or perfluorobenzoates react with α-(N-carbamoyl)alkylcuprates to afford scalemic α-(N-carbamoyl) allenes which undergo N-Boc deprotection and AgNO3-promoted cyclization to afford N-alkyl-3-pyrrolines. The synthetic sequence proceeds under optimal conditions with no loss of enantiopurity relative to the starting propargyl alcohols prepared by asymmetric addition of terminal alkynes to aldehydes.

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History

  • Published In Issue November 10, 2006
  • Received July 11, 2006

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