Copper catalyzed diastereoselective and enantioselective hydroborylation of cyclopentenylcarboxyesters

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...

Full description

Saved in:
Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2024-03, Vol.11 (7), p.2102-2107
Main Authors: Yao, Yufeng, Huang, Ming, Chen, Chunyu, Zeng, Hao, Li, Ze, Guo-Qiao, Lai, Zhang, Pinglu
Format: Article
Language:English
Subjects:
Copper
Enantiomers
Stereoselectivity
Substrates
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:2052-4110
2052-4110
DOI:10.1039/d4qo00114a