Synlett 2018; 29(13): 1749-1752
DOI: 10.1055/s-0037-1610172
letter
© Georg Thieme Verlag Stuttgart · New York

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

Emma K. Edelstein
Department of Chemistry, Boston College, Chestnut Hill, MA 02467, USA   Email: morken@bc.edu
,
Andrea C. Grote ◊
Department of Chemistry, Boston College, Chestnut Hill, MA 02467, USA   Email: morken@bc.edu
,
Maximilian D. Palkowitz ◊
Department of Chemistry, Boston College, Chestnut Hill, MA 02467, USA   Email: morken@bc.edu
,
James P. Morken*
Department of Chemistry, Boston College, Chestnut Hill, MA 02467, USA   Email: morken@bc.edu
› Author Affiliations

This work was supported by the NIH (NIGMS 59417).
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Publication History

Received: 03 April 2018

Accepted after revision: 11 May 2018

Publication Date:
20 June 2018 (online)


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These authors contributed equally this work

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.

Supporting Information