4.8 Article

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

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ORGANIC LETTERS
卷 15, 期 12, 页码 3082-3085

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AMER CHEMICAL SOC
DOI: 10.1021/ol401265a

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  1. Purdue University
  2. Midwest Crossroads Alliance for Graduate Education and the Professoriate

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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.

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