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手性硫代磷酸作为有机催化剂的设计、合成与评估

Design, synthesis, and evaluation of chiral thiophosphorus acids as organocatalysts.

作者信息

Winters Karen R, Montchamp Jean-Luc

机构信息

Department of Chemistry and Biochemistry, Texas Christian University, Fort Worth, Texas 76129, United States.

出版信息

Beilstein J Org Chem. 2022 Oct 17;18:1471-1478. doi: 10.3762/bjoc.18.154. eCollection 2022.

DOI:10.3762/bjoc.18.154
PMID:36320342
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9592963/
Abstract

A series of -stereogenic chiral phosphorus acids (CPAs) were synthesized to determine the requirements for efficient asymmetric organocatalysis. In order to eliminate the need for -symmetry in common CPAs, various scaffolds containing -symmetrical thiophosphorus acids were chosen. These new compounds were synthesized and evaluated in the asymmetric transfer hydrogenation of 2-phenylquinoline. Although the efficacy of the thiophosphorus acids was disappointing for this reaction, the work should be useful for developing structural design elements.

摘要

合成了一系列具有立体中心的手性磷酸(CPAs),以确定高效不对称有机催化的要求。为了消除常见CPAs中对对称的需求,选择了各种含有对称硫代磷酸的骨架。合成了这些新化合物,并在2-苯基喹啉的不对称转移氢化反应中进行了评估。尽管硫代磷酸对该反应的效果令人失望,但这项工作对于开发结构设计元素应该是有用的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/fed19dad9210/Beilstein_J_Org_Chem-18-1471-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/c520322f8625/Beilstein_J_Org_Chem-18-1471-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/49bf887ec5cf/Beilstein_J_Org_Chem-18-1471-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/2486e2c65187/Beilstein_J_Org_Chem-18-1471-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/bb3b94418858/Beilstein_J_Org_Chem-18-1471-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/8e7e8cac5dcc/Beilstein_J_Org_Chem-18-1471-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/c65266ce8713/Beilstein_J_Org_Chem-18-1471-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/214d22cb3841/Beilstein_J_Org_Chem-18-1471-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/fed19dad9210/Beilstein_J_Org_Chem-18-1471-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/c520322f8625/Beilstein_J_Org_Chem-18-1471-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/49bf887ec5cf/Beilstein_J_Org_Chem-18-1471-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/2486e2c65187/Beilstein_J_Org_Chem-18-1471-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/bb3b94418858/Beilstein_J_Org_Chem-18-1471-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/8e7e8cac5dcc/Beilstein_J_Org_Chem-18-1471-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/c65266ce8713/Beilstein_J_Org_Chem-18-1471-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/214d22cb3841/Beilstein_J_Org_Chem-18-1471-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dd16/9592963/fed19dad9210/Beilstein_J_Org_Chem-18-1471-g009.jpg

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