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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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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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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Sasmal, A
Taniguchi, T
Wipf, P
Curran, DPcurran@pitt.eduCURRAN
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


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