期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 35, 页码 10458-10462出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201605445
关键词
boron; cyanation; nucleophilic addition; reaction mechanisms; synthetic methods
资金
- Ministry of Education, Culture, Sports, Science, and Technology (MEXT), Japan [16K17868]
- Grants-in-Aid for Scientific Research [16K17868] Funding Source: KAKEN
The highly efficient electrophilic cyanation of boron enolates using readily available cyanating reagents, N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) and p-toluenesulfonyl cyanide (TsCN), is reported. Various b-ketonitriles were prepared by this new protocol, which has a remarkably broad substrate scope compared to existing methods. The present method also allowed efficient synthesis of b-ketonitriles containing a quaternary a-carbon center. In addition, a preliminary result with the use of a chiral boron enolate for the enantioselective cyanation reaction is described.
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