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-β-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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Bibliographic Details
Published inOrganic letters Vol. 12; no. 11; pp. 2650 - 2652
Main Authors Banerjee, Biplab, Litvinov, Dmitry N., Kang, Junghoon, Bettale, Jennifer D., Castle, Steven L.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.06.2010
Amer Chemical Soc
Subjects
Alkynes - chemistry
Amides - chemistry
Catalysis
Chemistry
Chemistry, Organic
Molecular Structure
Peptides, Cyclic - chemical synthesis
Peptides, Cyclic - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Sulfhydryl Compounds - chemistry
Thioamides - chemical synthesis
Thioamides - chemistry
RATES
APOPTOSIS INDUCER
CHIRAL YNAMIDES
CHEMISTRY
STREPTOMYCES-OLIVOVIRIDIS
N-ACYL CYANAMIDES
ALKYNES
THIOVIRIDAMIDE
CYCLIZATION
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Summary: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-β-thioenamide adducts in rapid fashion (10 min) and good dr, whereas employing excess thiol and longer reaction times favors the trans products.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol1008679