Catalyst-controlled reverse selectivity in C-C bond formation: NHC-Cu-catalyzed α-selective allylic alkylation with organolithium reagentsElectronic supplementary information (ESI) available: General procedures, optimization tables, experimental and spectroscopic data for all compounds. See DOI: 10.1039/c5cc01521a

An efficient and highly α-selective copper-catalyzed allylic alkylation of allylic halides with organolithium reagents is presented. The use of N-heterocyclic carbenes as ligands is key to reverse the common γ-selectivity of this transformation and gives rise to the corresponding linear products wit...

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Main Authors: Pizzolato, Stefano F, Giannerini, Massimo, Bos, Pieter H, Fañanás-Mastral, Martín, Feringa, Ben L
Format: Article
Language:English
Online Access:Get full text
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Summary:An efficient and highly α-selective copper-catalyzed allylic alkylation of allylic halides with organolithium reagents is presented. The use of N-heterocyclic carbenes as ligands is key to reverse the common γ-selectivity of this transformation and gives rise to the corresponding linear products with high levels of regioselectivity. An efficient and highly α-selective copper-catalyzed allylic alkylation of allylic halides with organolithium reagents is presented.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc01521a