A novel three-component reaction catalyzed by dirhodium(II) acetate: Decomposition of phenyldiazoacetate with arylamine and imine for highly diastereoselective synthesis of 1,2-diamines

被引：96
作者：
Wang, YH [1 ]
Zhu, YX
Chen, ZY
Mi, AQ
Hu, WH
Doyle, MP
机构：
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Key Lab Asymmetr Synth & Chirotechnol Sichuan Pro, Chengdu 610041, Peoples R China
[2] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 21期
关键词：
D O I：
10.1021/ol035490p
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] A practical highly diastereoselective synthesis of 1,2-diamines through carbon-carbon bond formation involving an ammonium ylide intermediate is reported for the first time. By treating methyl phenyldiazoacetate with arylamine and imine in the presence of dirhodium acetate, the erythro diastereomer of methyl 1,2-diaryl-1,2-diaminopropanoate is formed with stereochemical preferences greater than 10:1.
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页码：3923 / 3926
页数：4
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