relation: http://d-scholarship-dev.library.pitt.edu/22253/
title: Memory of chirality in rebound cyclizations of α-amide radicals
creator: Sasmal, A
creator: Taniguchi, T
creator: Wipf, P
creator: Curran, DP
description: 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.
date: 2013-01-02
type: Article
type: PeerReviewed
format: text/plain
language: en
rights: attached
identifier: http://d-scholarship-dev.library.pitt.edu/22253/1/licence.txt
identifier:   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     
relation: 10.1139/v2012-085