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Enantioselective Synthesis of Tertiary and Quaternary Stereogenic Centers: Copper/Phosphoramidite‐Catalyzed Allylic Alkylation with Organolithium Reagents
Author(s) -
FañanásMastral Martín,
Pérez Manuel,
Bos Pieter H.,
Rudolph Alena,
Harutyunyan Syuzanna R.,
Feringa Ben L.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201107840
Subject(s) - stereocenter , phosphoramidite , enantioselective synthesis , tsuji–trost reaction , alkylation , reagent , allylic rearrangement , combinatorial chemistry , chemistry , organic chemistry , catalysis , dna , biochemistry , oligonucleotide
An efficient and highly enantioselective copper‐catalyzed allylic alkylation of disubstituted allyl halides with primary and secondary organolithium reagents using phosphoramidite ligands is reported. The use of trisubstituted allyl bromides allows, for the first time, the enantioselective synthesis of all‐carbon quaternary stereogenic centers with these reactive organometallic reagents.