Convenient synthesis of stable aldimine-borane complexes, chiral delta-amino alcohols, and gamma-substituted GABA analogues from nitriles.
A one-pot synthesis of stable aldimine-trialkylborane adducts, the first synthesis of C- and N-deuterated imine-borane complexes, and their application for a highly enantioselective (84-99% ee) synthesis of delta-amino alcohols and gamma-substituted gamma-aminobutyric acids, including deuterated amino acids from nitriles, are described.
Ramachandran
P Veeraraghavan
PV
Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA. chandran@purdue.edu
Biswas
Debanjan
D
D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D001880:Boranes / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D000605:Amino Alcohols; D001880:Boranes; D007097:Imines; D009570:Nitriles; D005680:gamma-Aminobutyric Acid