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, E-mail: dieterrclemson.edu

R. K. Dieter, N. Chen, V. K. Gore, J. Org. Chem., 2006, 71, 8755-8760.

DOI: 10.1021/jo061442h

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Abstract

Enantioenriched propargyl mesylates or perfluorobenzoates react with α-(N-carbamoyl)alkylcuprates to afford scalemic α-(N-carbamoyl) allenes. Subsequent N-Boc deprotection and AgNO₃-promoted cyclization afford enantioenriched N-alkyl-3-pyrrolines.

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Key Words

Allenes, 3-Pyrrolines, tert-Butyl carbamates

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ID: J42-Y2006-3620