Highly stereoselective synthesis of (borylmethyl)cyclopropylamines by copper-catalyzed aminoboration of methylenecyclopropanes.
A Cu-catalyzed aminoboration of 1-methylenecyclopropanes with bis(pinacolato)diboron and O-benzoyl-N,N-dialkylhydroxylamines has been developed. The Cu catalysis provides a rapid and concise access to (borylmethyl)cyclopropylamines in a highly regio- and diastereoselective manner. The products obtained can be useful building blocks for the synthesis of potential antidepressants, trans-2-arylcyclopropylamine derivatives.
Department of Applied Chemistry, Faculty of Engineering, Osaka University , Suita, Osaka 565-0871, Japan.
Ryosuke
R
Sakae
Naoki
N
Matsuda
Koji
K
Hirano
Tetsuya
T
Satoh
Masahiro
M
Miura
D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001896:Boron Compounds; D003521:Cyclopropanes; C508672:methylenecyclopropane; D003300:Copper; C067351:cyclopropylamine