Catalytic Asymmetric Arylation of α-Aryl-α-diazoacetates with Aniline Derivatives

被引：144
作者：
Xu, Bin [1 ,2 ]
Li, Mao-Lin [1 ,2 ]
Zuo, Xiao-Dong [1 ,2 ]
Zhu, Shou-Fei [1 ,2 ,3 ]
Zhou, Qi-Lin [1 ,2 ,3 ]
机构：
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
[3] Nankai Univ, Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 27期
基金：
中国国家自然科学基金;
关键词：
C-H FUNCTIONALIZATION; CHIRAL DIRHODIUM(II) CARBOXYLATES; SPIRO PHOSPHORIC-ACIDS; INSERTION REACTION; BIOLOGICAL EVALUATION; CARBON INSERTION; GOLD CATALYSIS; CYCLIC ENONES; BONDS; INDOLES;
D O I：
10.1021/jacs.5b05086
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The asymmetric arylation of diazo compounds with aniline derivatives cooperatively catalyzed by an achiral dirhodium complex and a chiral spiro phosphoric acid is reported. The reaction provides a new method for the facile synthesis of a-diarylacetates, versatile building blocks with alpha-diaryl tertiary chiral center, in good yields (up to 95%) with high enantioselectivities (up to 97% ee). Preliminary mechanistic studies suggest that the arylation reaction proceeds via a stepwise process, in which the enantioselectivity is controlled by a chiral spiro phosphoric acid-promoted proton shift in a zwitterionic intermediate. This work represents the first asymmetric intermolecular C(sp(2))-H bond insertion reaction with arenes.
引用
收藏
页码：8700 / 8703
页数：4
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