Boroalkyl Group Migration Provides a Versatile Entry into α-Aminoboronic Acid Derivatives

被引：70
作者：
He, Zhi [1 ]
Zajdlik, Adam [1 ]
St Denis, Jeffrey D. [1 ]
Assem, Naila [1 ]
Yudin, Andrei K. [1 ]
机构：
[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 24期
基金：
加拿大自然科学与工程研究理事会;
关键词：
TRANSITION-STATE ANALOG; SUZUKI CROSS-COUPLINGS; AMIDE BOND FORMATION; ORGANOBORON COMPOUNDS; CARBOXYLIC-ACIDS; 2+2+2 CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; DIPHENYLPHOSPHORYL AZIDE; 8-QUINOLINEBORONIC ACID; CURTIUS REARRANGEMENT;
D O I：
10.1021/ja304173d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A reaction exemplifying migration of boron-substituted carbon is described. We show that alpha-boroalkyl groups of transient boroalkyl acyl azide intermediates readily migrate from carbon to nitrogen. This process allows access to a new class of stable molecules, alpha-boryl isocyanates, from alpha-borylcarboxylic acid precursors. The methodology facilitates synthesis of a wide range of alpha-aminoboronic acid derivatives, including alpha,alpha-disubstituted analogues.
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收藏
页码：9926 / 9929
页数：4
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