1995•Angewandte Chemie International Edition in EnglishRequires access
Lithium Intermediates during the α‐Lithiation and Subsequent α‐Substitution of Heterocyclic Amines in the Presence of CO2
Sarah C. Ball, Ian Cragg‐Hine, Matthew G. Davidson, Robert P. Davies, Andrew J. Edwards, I. López-Solera, Paul R. Raithby, Ronald Snaith
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Abstract
Two interdependent steps appear to be involved in the CO2-mediated electrophilic substitution of cyclic amines in the α position. The key finding is that the lithium carbamate 1 is not lithiated with tBuLi to any extent, but reacts only after addition of electrophiles like Me3SiCl to give the desired α-substitution product 2.