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- Title
Enantiodivergent Deprotonation/Acylation of α-Amino Nitriles.
- Authors
Sasaki, Michiko; Takegawa, Tomo; Sakamoto, Kunihiro; Kotomori, Yuri; Otani, Yuko; Ohwada, Tomohiko; Kawahata, Masatoshi; Yamaguchi, Kentaro; Takeda, Kei
- Abstract
Back to ‘base'ics: The title reaction of enantioenriched α‐ureidonitriles was found to proceed in a highly enantiodivergent manner despite the intermediacy of stereolabile α‐nitrile metallocarbanions. Enantiodivergence is dependent upon the base used. For the less basic hexamethyldisilazides (HMDS), deprotonation in which a metal (M) cation is precomplexed with an electrophile is proposed. LDA=lithium diisopropylamide.
- Subjects
ENANTIOSELECTIVE catalysis; CARBANIONS; NITRILE derivatives; CARBAMOYL compounds; PROTON transfer reactions; ACYLATION; CHEMICAL reactions; ANIONS
- Publication
Angewandte Chemie International Edition, 2013, Vol 52, Issue 49, p12956
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201306443