Issue 34, 2023

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

Abstract

A highly enantioselective rhodium-catalyzed reductive dearomatization of 7-substituted pyrazolo[1,5-a]pyrimidines has been realized for the first time by two strategies to afford chiral 4,5,6,7-tetrahydropyrazolo[1,5-a]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.

Graphical abstract: Highly enantioselective Rh-catalyzed asymmetric reductive dearomatization of multi-nitrogen polycyclic pyrazolo[1,5-a]pyrimidines

Supplementary files

Article information

Article type
Edge Article
Submitted
23 Apr 2023
Accepted
20 Jul 2023
First published
28 Jul 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 9048-9054

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

C. Xie, G. Xiao, Q. Guo, X. Wu, G. Zi, W. Ding and G. Hou, Chem. Sci., 2023, 14, 9048 DOI: 10.1039/D3SC02086J

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