Boroalkyl group migration provides a versatile entry into α-aminoboronic acid derivatives.
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.
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
Zhi
Z
He
Adam
A
Zajdlik
Jeffrey D
JD
St Denis
Naila
N
Assem
Andrei K
AK
Yudin
D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D001386:Azides / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D001897:Boronic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D017953:Isocyanates / Q000138:chemical synthesis / Q000737:chemistry
D000596:Amino Acids; D001386:Azides; D001896:Boron Compounds; D001897:Boronic Acids; D017953:Isocyanates; D002244:Carbon