Catalytic asymmetric direct α-alkylation of amino esters by aldehydes via imine activation

被引：112

作者：

Xu, Biao ^{[1
]}

Shi, Li-Li ^{[1
]}

Zhang, Yu-Zu ^{[1
]}

Wu, Zhi-Jun ^{[2
]}

Fu, Li-Na ^{[1
]}

Luo, Chun-Qin ^{[1
]}

Zhang, Lan-Xi ^{[1
]}

Peng, Yun-Gui ^{[1
]}

Guo, Qi-Xiang ^{[1
]}

机构：

[1] Southwest Univ, Sch Chem & Chem Engn, Chongqing 400715, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

来源：

CHEMICAL SCIENCE | 2014年 / 5卷 / 05期

关键词：

BRONSTED ACID CATALYSIS; ORGANIC CATALYSIS; ENAMINE CATALYSIS; CHIRAL KETONES; HYDROGEN-BONDS; ONE-POT; CYCLOADDITION; ALDOL; ORGANOCATALYSIS; CONDENSATION;

D O I：

10.1039/c3sc53314j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two types of BINOL-related chiral aldehydes were used as organocatalysts for the direct alpha-functionalization of N-unprotected amino esters. The first chiral aldehyde catalysed alpha-alkylation of 2-aminomalonates with 3-indolylmethanols via imine activation was reported. Various tryptophan derivatives were produced in good yields and with high enantioselectivities. A reasonable mechanism was proposed and the core intermediates were identified by high resolution mass spectroscopy (HRMS).

引用

页码：1988 / 1991

页数：4

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