Li, X and Curran, DP
(2010)
Diverging chemoselective reactions of separable amide rotational isomers.
Organic Letters, 12 (3).
612 - 614.
ISSN 1523-7060
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Abstract
[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.
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