Biphenol-based ligands for Cu-catalyzed asymmetric conjugate addition

作者:

A AlexakisD PoletC BenhaimS Rosset

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摘要:

The synthesis and characterization of seven new phosphoramidite ligands are described, as well as their use in copper-catalyzed 1,4-addition of diethylzinc to a wide range of substrates. Enantioselectivities of up to >99.5% are obtained.Graphic(5,7-Dioxa-6-phospha-dibenzo[,]cyclohepten-6-yl)-bis-()-(1-naphthalen-2-yl-ethyl)-amine36302Ee>99%[]=−404.9 ( 1.12, CHCl)Source of chirality: ()-1-Naphthalen-2-yl-ethylamineAbsolute configuration: (,)Bis-()-(1-naphthalen-2-yl-ethyl)-(2,4,8,10-tetramethyl-5,7-dioxa-6-phospha-dibenzo[,]cyclohepten-6-yl)-amine40382Ee>99%[]=−435.0 ( 1.0, CHCl)Source of chirality: ()-1-Naphthalen-2-yl-ethylamineAbsolute configuration: (,)Bis-()-(1-naphthalen-2-yl-ethyl)-(2,4,8,10-tetrachloro-5,7-dioxa-6-phospha-dibenzo[,]cyclohepten-6-yl)-amine362642Ee>99%[]=−417.0 ( 1.05, CHCl)Source of chirality: ()-1-Naphthalen-2-yl-ethylamineAbsolute configuration: (,)(4,8-Dimethoxy-2,10-dimethyl-5,7-dioxa-6-phospha-dibenzo[,]cyclohepten-6-yl)-bis-()-(1-naphthalen-2-yl-ethyl)-amine40384Ee>99%[]=−408.7 ( 1.05, CHCl)Source of chirality: ()-1-Naphthalen-2-yl-ethylamineAbsolute configuration: (,)(4,8-Diallyl-5,7-dioxa-6-phospha-dibenzo[,]cyclohepten-6-yl)-bis-()-(1-naphthalen-2-yl-ethyl)-amine42382Ee>99%[]=−347.0 ( 1.04, CHCl)Source of chirality: ()-1-Naphthalen-2-yl-ethylamineAbsolute configuration: (,)[4,8-Bis-(2-methyl-allyl)-5,7-dioxa-6-phospha-dibenzo[,]cyclohepten-6-yl]-bis-()-(1-naphthalen-2-yl-ethyl)-amine44422Ee>99%[]=−249.1 ( 1.06, CHCl)Source of chirality: ()-1-Naphthalen-2-yl-ethylamineAbsolute configuration: (,)Bis-()-(1-naphthalen-2-yl-ethyl)-(2,4,8,10-tetraphenyl-5,7-dioxa-6-phospha-dibenzo[,]cyclohepten-6-yl)-amine60462Ee>99%[]=−263.0 ( 1.00, CHCl)Source of chirality: ()-1-Naphthalen-2-yl-ethylamineAbsolute configuration: (,)

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DOI:

10.1016/j.tetasy.2004.05.016

被引量:

118

年份:

2004

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