%A X Li
%A DP Curran
%J Organic Letters
%T Diverging chemoselective reactions of separable amide rotational isomers
%X [Chemical equation presented] Diverging chemoselective reactions of a pair of amide rotamers have been observed by separating the rotamers and then reacting them individually. Reduction of (Z)-N-allyl-2-(phenylselanyl)-W-(2,4,6- tri-iert-butylphenyl)acetamide with tributyltin hydride at room temperature provides only the product of 5-exo cyclizatlon, 4-methyl-1-(2,4,6-tri-fert- butylphenyl)pyrrolidin-2-one. In contrast, reduction of the corresponding (E) amide rotational isomer under identical conditions provides only the reduced product, (E)-N-allyl-N-(2,4,6-tri-fert-butylphenyl)acetamide. Such diverging reactions of rotamers may be common in transformations involving reactive intermediates (carbenes, radicals, organometallic Intermediates) that have low barriers to onward reactions relative to amide rotation. ? 2010 American Chemical Society.
%N 3
%P 612 - 614
%V 12
%D 2010
%R 10.1021/ol902808m
%L pittir17322