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Asymmetric Conjugate Addition to α‐Halo Enones: Dramatic Effect of Styrene on the Enantioselectivity
Author(s) -
Li Kangying,
Alexakis Alexandre
Publication year - 2006
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.200602417
Subject(s) - conjugate , styrene , chemistry , scavenger , reagent , halo , enantioselective synthesis , addition reaction , catalysis , asymmetric induction , combinatorial chemistry , organic chemistry , radical , mathematics , copolymer , physics , polymer , mathematical analysis , quantum mechanics , galaxy
A simple trick could prove generally valuable for asymmetric copper‐catalyzed conjugate addition reactions. It was found that the enantioselectivities of such reactions of dialkyl zinc reagents with α‐halo enones in the presence of chiral phosphorimidite ligands were dramatically improved upon the addition of styrene, which acts as a radical scavenger to suppress the competitive non‐asymmetric radical pathway (see example).