by Michiko Sasaki, Tomo Takegawa, Kunihiro Sakamoto, Yuri Kotomori, Yuko Otani, Tomohiko Ohwada, Masatoshi Kawahata, Kentaro Yamaguchi, Kei Takeda*
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 metalocarbanions. 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.
Angewandte Chemie International Edition
DOI: 10.1002/anie.201306443
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