Memory of chirality in rebound cyclizations of α-amide radicals

Sasmal, A and Taniguchi, T and Wipf, P and Curran, DP (2013) Memory of chirality in rebound cyclizations of α-amide radicals. Canadian Journal of Chemistry, 91 (1). 1 - 5. ISSN 0008-4042

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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. © 2012 Published by NRC Research Press.

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Details

Item Type:	Article
Status:	Published
Creators/Authors:	Creators Email Pitt Username ORCID Sasmal, A Taniguchi, T Wipf, P Curran, DP curran@pitt.edu CURRAN
Date:	2 January 2013
Date Type:	Publication
Journal or Publication Title:	Canadian Journal of Chemistry
Volume:	91
Number:	1
Page Range:	1 - 5
DOI or Unique Handle:	10.1139/v2012-085
Schools and Programs:	Dietrich School of Arts and Sciences > Chemistry
Refereed:	Yes
ISSN:	0008-4042
Date Deposited:	18 Jul 2014 21:16
Last Modified:	02 Feb 2019 15:56
URI:	http://d-scholarship.pitt.edu/id/eprint/22253

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