Evaluation of chiral oxazolines for the highly enantioselective diethylzinc addition to N-(diphenylphosphinoyl) imines

被引:55
作者
Zhang, XM [1 ]
Zhang, HL [1 ]
Lin, WQ [1 ]
Gong, LZ [1 ]
Mi, AQ [1 ]
Cui, X [1 ]
Jiang, YZ [1 ]
Yu, KB [1 ]
机构
[1] Chinese Acad Sci, Union Lab Asymmetr Synth, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China
关键词
D O I
10.1021/jo0268862
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
On the basis of the principle that the incorporation of the structurally rigid and conformationally restricted skeleton in beta-amino alcohols is beneficial to the enantioselective diethylzinc addition to imines, a series of chiral oxazolines, which had been designed and conveniently prepared from commercially available (1S,2S)-2-amino-1-phenylpropane-1,3-diol, were applied in the diethylzinc addition to diphenylphosphinoyl imines to give high yields of 68-84% and excellent ee values of 90-95%. The configuration of the product was controlled by the chirality of the carbon bonded to the hydroxyl group in the oxazoline. Oxazolines bearing a para- or meta-substituted phenyl group generally offered higher enantioselectivity than those containing an ortho-substituted phenyl. The X-ray structures of 4f and 4j, in combination with the proposed transition state, preliminarily explained why oxazolines with a para- or meta-substituent on the phenyl group gave higher enantioselectivities than those bearing an ortho-substituent. This successful example using chiral oxazolines to promote the titled reaction implies that a large family of chiral compounds containing an oxazoline ring moiety have the potential to be developed for promoting the highly enantioselective dialkylzinc: addition to N-(diphenylphosphinoyl) imines.
引用
收藏
页码:4322 / 4329
页数:8
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