Stereoselective additions of thiyl radicals to terminal ynamides

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

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Amides / chemistry
  • Catalysis
  • Molecular Structure
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry*
  • Thioamides / chemical synthesis*
  • Thioamides / chemistry

Substances

  • Alkynes
  • Amides
  • Peptides, Cyclic
  • Sulfhydryl Compounds
  • Thioamides
  • thioviridamide