Enantioselective Cross-Coupling of meso-Epoxides with Aryl Halides

被引：160

作者：

Zhao, Yang ^{[1
]}

Weix, Daniel J. ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 09期

关键词：

KINETIC RESOLUTION; BOND FORMATION; CATALYST; LIGAND; COMPLEXES; RADICALS; DESYMMETRIZATION; COPOLYMERIZATION; AMINOLYSIS; GENERATION;

D O I：

10.1021/jacs.5b01909

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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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页码：3237 / 3240

页数：4

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