Enantiodivergent deprotonation/acylation of α-amino nitriles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2013)
摘要
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.
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关键词
asymmetric synthesis,carbanions,cyanides,lithium,metalation
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