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. 2018 Aug;29(13):1749-1752.
doi: 10.1055/s-0037-1610172. Epub 2018 Jun 20.

A Protocol for Direct Stereospecific Amination of Primary, Secondary, and Tertiary Alkylboronic Esters

Emma K Edelstein  1 , Andrea C Grote #  1 , Maximilian D Palkowitz #  1 , James P Morken  1
Affiliations

A Protocol for Direct Stereospecific Amination of Primary, Secondary, and Tertiary Alkylboronic Esters

Emma K Edelstein et al. Synlett. 2018 Aug.

Abstract

The direct, stereospecific amination of alkylboronic and borinic esters can be conducted by treatment of the organoboron compound with methoxyamine and potassium tert-butoxide. In addition to being stereospecific, this process also enables the direct amination of tertiary boronic esters in an efficient fashion.

Keywords: Amination; Asymmetric Synthesis; Chiral Amines; Organoboron; Stereochemistry.

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Figures

Scheme 1
Scheme 1
Amination of Alkylboronic Esters.
Scheme 2.
Scheme 2.
Prospective Mechanisms for Boronic Ester Amination.
Scheme 3.
Scheme 3.
Substrate Scope in the Amination of Primary and Secondary Alkylboronic Esters. (a) Experiment conducted with 5 equiv. MeONH2 and 7 equiv KOtBu.
Scheme 4.
Scheme 4.
Amination of Tertiary Boronic Esters. (a) Using work-up procedure A, the primary amine was isolated. (b) Using work-up procedure B, the product was isolated as the Boc-protected amine.
Scheme 5.
Scheme 5.
Preparative Amination Reactions.
See this image and copyright information in PMC

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