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Org Lett. 2010 Jun 4;12(11):2650-2. doi: 10.1021/ol1008679.

Stereoselective additions of thiyl radicals to terminal ynamides.

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  • 1Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.

Abstract

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.

PMID:
20438051
PMCID:
PMC2878391
DOI:
10.1021/ol1008679
[PubMed - indexed for MEDLINE]
Free PMC Article
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