Memory of chirality in rebound cyclizations of α-amide radicals-Reference-Cited by-同舟云学术

Memory of chirality in rebound cyclizations of α-amide radicals

Published:2013-01 Issue:1 Volume:91 Page:1-5
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Sasmal Aniruddha¹,Taniguchi Tsuyoshi¹,Wipf Peter¹,Curran Dennis P.¹

Affiliation:

1. Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.

Abstract

Reduction of (S)-N-(2-bromoallyl)-N-(tert-butyl)-2-methyl-3-phenylpropanamide with tributyltin hydride provides (3S,4S)-3-benzyl-1-(tert-butyl)-3,4-dimethylpyrrolidin-2-one with about 80% retention of chirality at the stereocenter adjacent to the amide carbonyl group. This memory of chirality is suggested to occur by transfer of chirality from a stereocenter to an axis, then from the axis back to a new stereocenter.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v2012-085

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