1380504-22-2Relevant academic research and scientific papers
Access to Cyclic Amino Boronates via Rhodium-Catalyzed Functionalization of Alkyl MIDA Boronates
St. Denis, Jeffrey D.,Lee, C. Frank,Yudin, Andrei K.
supporting information, p. 5764 - 5767 (2015/12/11)
Herein, we describe the rhodium-catalyzed C-H amination reaction of 1,2-boryl sulfamate esters derived from amphoteric α-boryl aldehydes. Depending on the substitution pattern of the boryl sulfamate ester, a diverse range of five- or six-membered ring heterocycles are accessible using this transformation. The highly chemoselective nature of the C-H functionalization reaction preserves the alkyl boronate functional group, which enables the synthesis of B-C-N and B-C-C-N motifs that are present in a number of hydrolase inhibitors.
Boroalkyl group migration provides a versatile entry into α-aminoboronic acid derivatives
He, Zhi,Zajdlik, Adam,St. Denis, Jeffrey D.,Assem, Naila,Yudin, Andrei K.
supporting information; experimental part, p. 9926 - 9929 (2012/08/07)
A reaction exemplifying migration of boron-substituted carbon is described. We show that α-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, α-boryl isocyanates, from α-borylcarboxylic acid precursors. The methodology facilitates synthesis of a wide range of α-aminoboronic acid derivatives, including α,α-disubstituted analogues.
