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Synthesis 2014; 46(04): 445-454
DOI: 10.1055/s-0033-1340502
DOI: 10.1055/s-0033-1340502
practical synthetic procedures
Efficient Preparation of α-Aminoboronic Acid Derivatives via Boroalkyl Group Migration
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.
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Reviews:
Recent modification of the Curtius rearrangement:
Acid-catalyzed reactions of hindered isocyanates with alcohols: