Organic letters

Dialkylaluminum N, O-Dimethylhydroxylamine Complex as a Reagent to Mask Reactive Carbonyl Groups in Situ from Nucleophiles

FJ Barrios, X Zhang, DA Colby

Index: Barrios, Francis J.; Zhang, Xuechao; Colby, David A. Organic Letters, 2010 , vol. 12, # 23 p. 5588 - 5591

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Citation Number: 6

Abstract

Aluminum complexes of N, O-dimethylhydroxylamine are effective reagents to mask carbonyl groups in situ from nucleophilic addition by organolithiums, Grignard reagents, and borohydrides. The utility of this process by selectively adding nucleophiles into carbonyl groups on a variety of structures as well as distinguishing between carbonyl groups on a sensitive natural product is demonstrated. 1H NMR analysis supports the in situ masking ...