Issue 7, 2024

Copper catalyzed diastereoselective and enantioselective hydroborylation of cyclopentenylcarboxyesters

Abstract

The optically-enriched cyclopentylborane derivatives containing consecutive stereogenic centers are of great use for the construction of chiral cyclopentanes. The preceding examples are limited to specialized substrates and suffer from a lack of generality, and the access to consecutive stereogenic centers remains elusive. Here we disclose a copper catalyzed conjugative borylation of cyclopentenylcarboxyesters, for accessing cyclopentyl boronates bearing a consecutive stereogenic center in a diastereoselective and enantioselective fashion. This method could be scaled up and the C–B bond in products could be easily transformed in late-stage functionalization. Furthermore, modeling for rationalization of the enantioselectivity and diastereoselectivity is proposed, which suggested that borylcupration is probably the enantio-determining step while the proton-decupration is the diastereo-determining step.

Graphical abstract: Copper catalyzed diastereoselective and enantioselective hydroborylation of cyclopentenylcarboxyesters

Supplementary files

Article information

Article type
Research Article
Submitted
18 Jan 2024
Accepted
18 Feb 2024
First published
20 Feb 2024

Org. Chem. Front., 2024,11, 2102-2107

Copper catalyzed diastereoselective and enantioselective hydroborylation of cyclopentenylcarboxyesters

Y. Yao, M. Huang, C. Chen, H. Zeng, Z. Li, G. Lai and P. Zhang, Org. Chem. Front., 2024, 11, 2102 DOI: 10.1039/D4QO00114A

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