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- Title
Electrophilic Cyanation of Boron Enolates: Efficient Access to Various β-Ketonitrile Derivatives.
- Authors
Kiyokawa, Kensuke; Nagata, Takaya; Minakata, Satoshi
- Abstract
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 β-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 β-ketonitriles containing a quaternary α-carbon center. In addition, a preliminary result with the use of a chiral boron enolate for the enantioselective cyanation reaction is described.
- Subjects
NITRILE derivatives; ELECTROPHILES; BORON compounds; TOLUENESULFONAMIDES; ENANTIOSELECTIVE catalysis; NUCLEOPHILIC addition (Chemistry)
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 35, p10458
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201605445