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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