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模块化设计的有机催化剂催化的对映选择性曼尼希反应。

Enantioselective -Mannich reaction catalyzed by modularly designed organocatalysts.

作者信息

Konda Swapna, Zhao John C-G

机构信息

Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA.

出版信息

Tetrahedron. 2018 Oct 18;74(42):6166-6172. doi: 10.1016/j.tet.2018.09.006. Epub 2018 Sep 5.

DOI:10.1016/j.tet.2018.09.006
PMID:30923409
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6433386/
Abstract

A highly stereoselective method for achieving the -Mannich reaction of aldehydes and ketones with ethyl (4-methoxyphenylimino)acetate was realized using the modularly designed organocatalysts (MDOs) self-assembled from cinchona alkaloid derivatives and (A)-pyrrolidien-3-carboxylic acid in the reaction media. The desired -Mannich products were obtained in good to excellent yields (up to 93%), excellent diastereoselectivities (up to 99:1 dr), and good to high enantioselectivities (up to 99% ee).

摘要

通过在反应介质中使用由金鸡纳生物碱衍生物和(A)-吡咯烷-3-羧酸自组装而成的模块化设计有机催化剂(MDOs),实现了一种用于醛和酮与(4-甲氧基苯基亚氨基)乙酸乙酯进行-Mannich反应的高度立体选择性方法。所需的-Mannich产物以良好至优异的产率(高达93%)、优异的非对映选择性(高达99:1 dr)和良好至高的对映选择性(高达99% ee)得到。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/931f/6433386/20d60dc0029c/nihms-1506126-f0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/931f/6433386/20d60dc0029c/nihms-1506126-f0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/931f/6433386/20d60dc0029c/nihms-1506126-f0001.jpg

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