4.8 Article

Stereoselective Additions of Thiyl Radicals to Terminal Ynamides

Journal

ORGANIC LETTERS
Volume 12, Issue 11, Pages 2650-2652

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol1008679

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Funding

  1. National Institutes of Health [GM70483]
  2. Brigham Young University (Cancer Research Center)

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Two complementary sets of conditions for radical additions of thiols to terminal ynamides are described. The use of 1 equiv of thiol affords the cis-beta-thioenamide adducts in rapid fashion (10 min) and good dr, whereas employing excess thiol and longer reaction times favors the trans products.

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