Catalytic enantioselective addition of organometallic reagents to N-formylimines using monodentate phosphoramidite ligands
摘要:
The asymmetric synthesis of protected amines via the copper/phosphoramidite-catalyzed addition of organozinc and organoaluminum reagents to N-acylimines, generated in situ from aromatic and aliphatic alpha-amidosulfones, is reported. High yields of optically active N-formyl-protected amines and enantioselectivities up to 99% were obtained. Under the reaction conditions, partial oxidation of the phosphoramidite ligand to the corresponding phosphoric amide was detected. A preliminary study on the origin and the effect on the catalytic addition reaction is presented.
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关键词:
ALPHA-CHIRAL AMINES ASYMMETRIC ADDITION DIORGANOZINC REAGENTS CONJUGATE ADDITION ORGANOLITHIUM REAGENTS DIETHYLZINC ADDITION N-(DIPHENYLPHOSPHINOYL) IMINES NUCLEOPHILIC-ADDITION AMIDOPHOSPHINE LIGAND ZEROVALENT PALLADIUM
DOI:
10.1021/jo702140f
年份:
2008
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