title: Control of transient aluminum-aminals for masking and unmasking reactive carbonyl groups.
abstract: 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.
authors.affiliation: Department of Chemistry and Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University , West Lafayette, Indiana 47907, United States.
authors.forename: Francis J
authors.initials: FJ
authors.lastname: Barrios
authors.forename: Brannon C
authors.initials: BC
authors.lastname: Springer
authors.forename: David A
authors.initials: DA
authors.lastname: Colby
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000535:Aluminum / Q000737:chemistry*; D004123:Dimethylamines / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D004123:Dimethylamines; D007202:Indicators and Reagents; D009942:Organometallic Compounds; C558817:N,O-dimethylhydroxylamine; D000535:Aluminum