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High Diversity on Simple Substrates: 1,4‐Dihalo‐2‐butenes and Other Difunctionalized Allylic Halides for Copper‐Catalyzed S N 2′ Reactions
Author(s) -
Falciola Caroline A.,
Alexakis Alexandre
Publication year - 2008
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.200801309
Subject(s) - allylic rearrangement , regioselectivity , chemistry , olefin fiber , reagent , catalysis , tsuji–trost reaction , alkylation , enantioselective synthesis , substitution reaction , medicinal chemistry , organic chemistry
Enantioselective allylic alkylation with an organomagnesium reagent catalyzed by copper thiophene carboxylate (CuTC) was carried out on difunctionalized substrates, such as commercially available 1,4‐dichloro‐2‐butene and 1,4‐dibromo‐2‐butene, and on similar compounds of higher substitution pattern of the olefin for the formation of all‐carbon chiral quaternary centers. The high regioselectivity obtained throughout the reactions favored good regiocontrol for the addition of phenyl Grignard reagents. Other difunctionalized substrates (allylic ethers and allylic alcohols) also underwent asymmetric S N 2′ substitution.