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手性伯胺-水杨酰胺催化的醛与马来酰亚胺的对映选择性迈克尔加成。

Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide.

机构信息

Departamento de Química Orgánica, Facultad de Ciencias, and Instituto de Síntesis Orgánica (ISO), Uni-versidad de Alicante, Apdo. 99, 03080 Alicante, Spain.

Departamento de Química Orgánica I, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain.

出版信息

Molecules. 2018 Dec 12;23(12):3299. doi: 10.3390/molecules23123299.

DOI:10.3390/molecules23123299
PMID:30545145
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6320823/
Abstract

A primary amine-salicylamide derived from chiral -cyclohexane-1,2-diamine was used as an organocatalyst for the enantioselective conjugate addition of aldehydes, mainly α,α-disubstituted to -substituted maleimides. The reaction was performed in toluene as a solvent at room temperature. The corresponding enantioenriched adducts were obtained with high yields and enantioselectivities up to 94%. Theoretical calculations were used to justify the stereoinduction.

摘要

一种由手性 -环己烷-1,2-二胺衍生的伯胺-水杨酰胺被用作有机催化剂,用于醛的对映选择性共轭加成,主要是 α,α-二取代到 -取代马来酰亚胺。反应在甲苯溶剂中于室温下进行。相应的对映体富集加成产物以高产率和高达 94%的对映选择性获得。理论计算用于证明立体诱导。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c694/6320823/989a8d5beadf/molecules-23-03299-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c694/6320823/be2307e85570/molecules-23-03299-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c694/6320823/a3b18e89b417/molecules-23-03299-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c694/6320823/bdad4dd525ce/molecules-23-03299-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c694/6320823/cf39f525a4ee/molecules-23-03299-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c694/6320823/989a8d5beadf/molecules-23-03299-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c694/6320823/be2307e85570/molecules-23-03299-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c694/6320823/a3b18e89b417/molecules-23-03299-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c694/6320823/bdad4dd525ce/molecules-23-03299-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c694/6320823/cf39f525a4ee/molecules-23-03299-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c694/6320823/989a8d5beadf/molecules-23-03299-g005.jpg

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J Org Chem. 2018 Sep 7;83(17):10318-10325. doi: 10.1021/acs.joc.8b01454. Epub 2018 Jul 11.
2
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Chemistry. 2022 Mar 28;28(18):e202200215. doi: 10.1002/chem.202200215. Epub 2022 Feb 28.
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