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铑催化多氮多环吡唑并[1,5 - ]嘧啶的高度对映选择性不对称还原脱芳构化反应

Highly enantioselective Rh-catalyzed asymmetric reductive dearomatization of multi-nitrogen polycyclic pyrazolo[1,5-]pyrimidines.

作者信息

Xie Chaochao, Xiao Guiying, Guo Qianling, Wu Xiaoxue, Zi Guofu, Ding Wanjian, Hou Guohua

机构信息

Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University No. 19 Xinjiekouwai St. Beijing 100875 China

Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University Shanghai 200240 China.

出版信息

Chem Sci. 2023 Jul 28;14(34):9048-9054. doi: 10.1039/d3sc02086j. eCollection 2023 Aug 30.

DOI:10.1039/d3sc02086j
PMID:37655036
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10466315/
Abstract

A highly enantioselective rhodium-catalyzed reductive dearomatization of 7-substituted pyrazolo[1,5-]pyrimidines has been realized for the first time by two strategies to afford chiral 4,5,6,7-tetrahydropyrazolo[1,5-]pyrimidines with excellent enantioselectivities of up to 98% ee. This method also provides an efficient approach for the synthesis of the powerful BTK inhibitor, zanubrutinib.

摘要

首次通过两种策略实现了铑催化的7-取代吡唑并[1,5 -]嘧啶的高度对映选择性还原脱芳构化反应，以高达98% ee的优异对映选择性得到手性4,5,6,7-四氢吡唑并[1,5 -]嘧啶。该方法还为强效BTK抑制剂泽布替尼的合成提供了一种有效途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec52/10466315/7180bc29a27b/d3sc02086j-s6.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec52/10466315/7180bc29a27b/d3sc02086j-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec52/10466315/6bc7dc768093/d3sc02086j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec52/10466315/1df13a3ff8ce/d3sc02086j-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec52/10466315/3c6bb0eb07b7/d3sc02086j-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec52/10466315/a3d82dc23bb5/d3sc02086j-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec52/10466315/8d2d99e18765/d3sc02086j-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec52/10466315/ab244fecd888/d3sc02086j-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec52/10466315/dd4e65534c61/d3sc02086j-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ec52/10466315/7180bc29a27b/d3sc02086j-s6.jpg

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