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C 1 ‐Symmetric Monosubstituted Chiral Diene Ligands in Asymmetric Rhodium‐Catalyzed 1,4‐Addition Reactions
Author(s) -
Gendrineau Thomas,
Chuzel Olivier,
Eijsberg Hendrik,
Genet JeanPierre,
Darses Sylvain
Publication year - 2008
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.200803230
Subject(s) - rhodium , diene , chemistry , adduct , catalysis , yield (engineering) , enantioselective synthesis , boronic acid , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , natural rubber , metallurgy
One trumps two : Monosubstituted chiral bicyclo[2.2.2]octadiene ligands, derived from carvone, form complexes with rhodium to catalyze the asymmetric addition of boronic acid substrates to α,β‐unsaturated ketones (see scheme). The 1,4‐adducts are produced in good yield and high enantioselectivity.