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通过铑催化的γ-丁烯内酯和γ-羟基丁烯内酯的不对称氢化反应简便地获得手性γ-丁内酯

Facile access to chiral γ-butyrolactones rhodium-catalysed asymmetric hydrogenation of γ-butenolides and γ-hydroxybutenolides.

作者信息

Zhou Yuxuan, Guo Siyuan, Huang Qiyuan, Lang Qiwei, Chen Gen-Qiang, Zhang Xumu

机构信息

Shenzhen Grubbs Institute, Department of Chemistry, and Medi-Pingshan, Southern University of Science and Technology Shenzhen 518000 People's Republic of China

Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology Shenzhen 518000 People's Republic of China.

出版信息

Chem Sci. 2023 Apr 15;14(18):4888-4892. doi: 10.1039/d3sc00491k. eCollection 2023 May 10.

DOI:10.1039/d3sc00491k
PMID:37181773
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10171041/
Abstract

The highly efficient Rh/ZhaoPhos-catalysed asymmetric hydrogenation of γ-butenolides and γ-hydroxybutenolides was successfully developed. This protocol provides an efficient and practical approach to the synthesis of various chiral γ-butyrolactones, which are synthetically valuable building blocks of diverse natural products and therapeutic substances, with excellent results (up to >99% conversion and 99% ee). Further follow-up transformations have been revealed to accomplish creative and efficient synthetic routes for several enantiomerically enriched drugs this catalytic methodology.

摘要

成功开发了铑/赵磷催化的γ-丁烯内酯和γ-羟基丁烯内酯的高效不对称氢化反应。该方法为合成各种手性γ-丁内酯提供了一种有效且实用的途径，这些γ-丁内酯是多种天然产物和治疗物质中具有合成价值的构建单元，反应结果优异（转化率高达>99%，对映体过量值高达99%）。进一步的后续转化已被揭示，以通过这种催化方法为几种对映体富集的药物完成创新且高效的合成路线。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd1/10171041/b6f9056a873b/d3sc00491k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd1/10171041/dcccadbc70ee/d3sc00491k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd1/10171041/bd9407da729f/d3sc00491k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd1/10171041/b6f9056a873b/d3sc00491k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd1/10171041/dcccadbc70ee/d3sc00491k-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd1/10171041/bd9407da729f/d3sc00491k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0cd1/10171041/b6f9056a873b/d3sc00491k-s2.jpg

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