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Diverging chemoselective reactions of separable amide rotational isomers

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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[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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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Li, X
Curran, DPcurran@pitt.eduCURRAN
Date: 5 February 2010
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 12
Number: 3
Page Range: 612 - 614
DOI or Unique Handle: 10.1021/ol902808m
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
PubMed ID: 20038129
Date Deposited: 14 Feb 2013 22:06
Last Modified: 02 Feb 2019 13:55


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