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Relaying asymmetry of transient atropisomers of o-iodoanilides by radical cyclizations

Petit, M and Lapierre, AJB and Curran, DP (2005) Relaying asymmetry of transient atropisomers of o-iodoanilides by radical cyclizations. Journal of the American Chemical Society, 127 (43). 14994 - 14995. ISSN 0002-7863

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Abstract

Atropisomers of N-2°-alkyl-N-acryloyl-2-iodoanlides have been resolved by chromatography and crystallization-induced asymmetric transformation. These molecules have atropisomerization barriers of 23-24 kcal/mol and return to equilibrium ratios over several hours at ambient temperature in solution. The transient chirality can be locked in by radical cyclizations, which provide N-2°-alkyl-3-methyl-1,3-dihydroindol-2-ones with high levels of chirality transfer. The mechanistic model features a stereoselective aryl radical cyclization that is more rapid than the rotation of the N-aryl bond of the anilide. Copyright © 2005 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Petit, M
Lapierre, AJB
Curran, DPcurran@pitt.eduCURRAN
Date: 2 November 2005
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 127
Number: 43
Page Range: 14994 - 14995
DOI or Unique Handle: 10.1021/ja055666d
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
PubMed ID: 16248616
Date Deposited: 15 Jul 2013 19:55
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/19320

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