Synthesis 2014; 46(04): 445-454
DOI: 10.1055/s-0033-1340502
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Efficient Preparation of α-Aminoboronic Acid Derivatives via Boroalkyl Group Migration

Adam Zajdlik
,
Zhi He
,
Jeffrey D. St Denis
,
Andrei K. Yudin*
Further Information

Publication History

Received: 05 November 2013

Accepted after revision: 09 December 2013

Publication Date:
21 January 2014 (online)


Abstract

A reaction demonstrating migration of boron-substituted carbon is presented. It is shown that α-boroalkyl groups of transient boroalkyl acyl azide intermediates migrate readily from carbon to nitrogen. This transformation allows access to a novel class of stable molecules, α-boryl isocyanates, from easily preparable α-borylcarboxylic acid precursors. The protocol enables the synthesis of a diverse range of α-aminoboronic acid derivatives, including α,α-disubstituted analogues.