Direct Amination of Alkyl and Aryl Pinacol Boronates

Paul Knochel; Nadja M. Barl

doi:10.1055/s-0032-1317730

Synfacts, Table of Contents

Synfacts 2013; 9(1): 0086
DOI: 10.1055/s-0032-1317730

Metal-Mediated Synthesis

Direct Amination of Alkyl and Aryl Pinacol Boronates

Authors

Paul Knochel
Nadja M. Barl

Abstract

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Mlynarski SN, Karns AS, Morken JP * Boston College, Chestnut Hill, USA
Direct Stereospecific Amination of Alkyl and Aryl Pinacol Boronates.

J. Am. Chem. Soc. 2012;
134: 16449-16451

Key words

boron - lithium - direct amination - pinacol boronates

Significance

Herein, the direct and stereospecific amination of various aryl and alkyl pinacol boronates with lithiated methoxyamine is disclosed. The corresponding (un)protected amines are obtained in very good yield and, in case of chiral compounds, with high enantiomeric excess.

Comment

Sensitive functional groups such as CN, OMe and CF₃ moieties are well tolerated with this methodology. In addition, this strategy might even be applied to gram-scale reactions without any further drawbacks.

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