%A A Sasmal
%A T Taniguchi
%A P Wipf
%A DP Curran
%J Canadian Journal of Chemistry
%T Memory of chirality in rebound cyclizations of ?-amide radicals
%X 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.
%N 1
%P 1 - 5
%V 91
%D 2013
%R 10.1139/v2012-085
%L pittir22253