期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 137, 期 9, 页码 3237-3240出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b01909
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资金
- NIH [R01 GM097243]
- University of Rochester
The first enantioselective cross-electrophile coupling of aryl bromides with meso-epoxides to form trans-beta-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.
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