1329422-36-7Relevant academic research and scientific papers
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.
Amphoteric α-boryl aldehydes
He, Zhi,Yudin, Andrei K.
, p. 13770 - 13773 (2011/10/05)
A new class of stable molecules, α-boryl aldehydes, has been prepared from oxiranyl N-methyliminodiacetyl boronates by a 1,2-boryl migration with concomitant epoxide scission. A range of boryl imines, alkenes, alcohols, acids, enol ethers, enamides, and other functionalized boronic acid derivatives that are difficult or impossible to prepare using established protocols can be accessed from α-boryl aldehydes. The chemoselective transformations of these building blocks, including the facile synthesis of functionalized unnatural amino acids from silyloxy and amido vinyl boronates, attest to the potential of α-boryl aldehydes in chemical synthesis.
