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Fluoro-Julia olefination as a mild, high-yielding route to alpha-fluoro acrylonitriles.

ABSTRACT: Synthesis of a novel, stable reagent (1,3-benzothiazol-2-ylsulfonyl)fluoroacetonitrile from readily synthesized ethyl alpha-(1,3-benzothiazol-2-ylsulfanyl)-alpha-fluoroacetate is reported. Aldehydes undergo condensations with (1,3-benzothiazol-2-ylsulfonyl)fluoroacetonitrile in the presence of DBU leading to alpha-fluoro acrylonitriles in high yields and with good Z-stereoselectivity. Lowering of reaction temperature increases the Z selectivity.

SUBMITTER: del Solar M

PROVIDER: S-EPMC2771215 | biostudies-literature | 2008 Nov

REPOSITORIES: biostudies-literature

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Fluoro-Julia olefination as a mild, high-yielding route to alpha-fluoro acrylonitriles.

del Solar Maria M Ghosh Arun K AK Zajc Barbara B

The Journal of organic chemistry 20081008 21

Synthesis of a novel, stable reagent (1,3-benzothiazol-2-ylsulfonyl)fluoroacetonitrile from readily synthesized ethyl alpha-(1,3-benzothiazol-2-ylsulfanyl)-alpha-fluoroacetate is reported. Aldehydes undergo condensations with (1,3-benzothiazol-2-ylsulfonyl)fluoroacetonitrile in the presence of DBU leading to alpha-fluoro acrylonitriles in high yields and with good Z-stereoselectivity. Lowering of reaction temperature increases the Z selectivity. ...[more]

PMID: 18841918

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