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Stereoselective additions of thiyl radicals to terminal ynamides.

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.

SUBMITTER: Banerjee B

PROVIDER: S-EPMC2878391 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Stereoselective additions of thiyl radicals to terminal ynamides.

Banerjee Biplab B Litvinov Dmitry N DN Kang Junghoon J Bettale Jennifer D JD Castle Steven L SL

Organic letters 20100601 11

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. ...[more]

PMID: 20438051

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