Stereoselective additions of thiyl radicals to terminal ynamides.
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.
Banerjee
Biplab
B
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.
Litvinov
Dmitry N
DN
Kang
Junghoon
J
Bettale
Jennifer D
JD
Castle
Steven L
SL
D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013854:Thioamides / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D000577:Amides; D010456:Peptides, Cyclic; D013438:Sulfhydryl Compounds; D013854:Thioamides; C509635:thioviridamide