Premium
Asymmetric Allylic Alkylation of Acyclic Allylic Ethers with Organolithium Reagents
Author(s) -
Pérez Manuel,
FañanásMastral Martín,
Hornillos Valentín,
Rudolph Alena,
Bos Pieter H.,
Harutyunyan Syuzanna R.,
Feringa Ben L.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202251
Subject(s) - tsuji–trost reaction , allylic rearrangement , reagent , enantioselective synthesis , phosphoramidite , chemistry , alkylation , catalysis , organic chemistry , organolithium compounds , combinatorial chemistry , lewis acids and bases , dna , biochemistry , oligonucleotide , ion , deprotonation
A highly efficient, regio‐ and enantioselective Cu I /phosphoramidite‐catalyzed asymmetric allylic alkylation of allyl ethers with organolithium reagents is reported (see scheme). The use of organolithium reagents is essential for this catalytic CC bond formation due to their compatibility with different Lewis acids. The versatility of allylic ethers under the copper‐catalyzed reaction conditions with organolithium reagents is demonstrated in the shortest synthesis of ( S )‐Arundic acid.