Asymmetric synthesis of primary amines via the spiroborate-catalyzed borane reduction of oxime ethers.
[reaction: see text] The enantioselective borane reduction of O-benzyloxime ethers to primary amines was studied under catalytic conditions using the spiroborate esters 5-10 derived from nonracemic 1,2-amino alcohols and ethylene glycol. Effective catalytic conditions were achieved using only 10% of catalyst 5 derived from diphenylvalinol in dioxane at 0 degrees C resulting in complete conversion to the corresponding primary amine in up to 99% ee.
Huang
Xiaogen
X
Department of Chemistry, University of Puerto Rico-Humacao, CUH Station, Humacao, Puerto Rico 00791.
Ortiz-Marciales
Margarita
M
Huang
Kun
K
Stepanenko
Viatcheslav
V
Merced
Francisco G
FG
Ayala
Angel M
AM
Correa
Wildeliz
W
Jesús
Melvin De
MD
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010091:Oximes / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D000605:Amino Alcohols; D001880:Boranes; D001881:Borates; D004987:Ethers; D010091:Oximes; D013141:Spiro Compounds