American Chemical Society
ol401265a_si_001.pdf (1.75 MB)

Control of Transient Aluminum–Aminals for Masking and Unmasking Reactive Carbonyl Groups

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journal contribution
posted on 2016-02-19, 05:31 authored by Francis J. Barrios, Brannon C. Springer, David A. Colby
A new reagent, the dimethylaluminum N,O-dimethylhydroxylamine complex, is effective at masking reactive carbonyl groups in situ from nucleophilic addition. This reagent allows chemoselective addition of reducing reagents, Grignard reagents, organolithiums, Wittig reagents, and enolates into substrates with multiple carbonyl groups. Moreover, the trapped carbonyl group, a stable aminal, can be unmasked in situ for additional synthetic manipulations.