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Enantioselective cross-coupling of meso-epoxides with aryl halides.

ABSTRACT: The first enantioselective cross-electrophile coupling of aryl bromides with meso-epoxides to form trans-?-arylcycloalkanols is presented. The reaction is catalyzed by a combination of (bpy)NiCl2 and a chiral titanocene under reducing conditions. Yields range from 57 to 99% with 78-95% enantiomeric excess. The 30 examples include a variety of functional groups (ether, ester, ketone, nitrile, ketal, trifluoromethyl, sulfonamide, sulfonate ester), both aryl and vinyl halides, and five- to seven-membered rings. The intermediacy of a carbon radical is strongly suggested by the conversion of cyclooctene monoxide to an aryl [3.3.0]bicyclooctanol.

SUBMITTER: Zhao Y

PROVIDER: S-EPMC4415026 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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Enantioselective cross-coupling of meso-epoxides with aryl halides.

Zhao Yang Y Weix Daniel J DJ

Journal of the American Chemical Society 20150302 9

The first enantioselective cross-electrophile coupling of aryl bromides with meso-epoxides to form trans-β-arylcycloalkanols is presented. The reaction is catalyzed by a combination of (bpy)NiCl2 and a chiral titanocene under reducing conditions. Yields range from 57 to 99% with 78-95% enantiomeric excess. The 30 examples include a variety of functional groups (ether, ester, ketone, nitrile, ketal, trifluoromethyl, sulfonamide, sulfonate ester), both aryl and vinyl halides, and five- to seven-me ...[more]

PMID: 25716775

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