C-1-symmetric monosubstituted chiral diene ligands in asymmetric rhodium-catalyzed 1,4-addition reactions

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. The 1,4-adducts are produced in good yield and high enantioselectivity.

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 47; no. 40; pp. 7669 - 7672
Main Authors Gendrineau, Thomas, Chuzel, Olivier, Eijsberg, Hendrik, Genet, Jean-Pierre, Darses, Sylvain
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 22.09.2008
Wiley-VCH Verlag
Subjects
Chemical Sciences
Chemistry
Chemistry, Multidisciplinary
Organic chemistry
Physical Sciences
Science & Technology
Michael addition
HIGH-PERFORMANCE
STEERING LIGANDS
COMPLEXES
ALDEHYDES
ARYLBORONIC ACIDS
BORONIC ACIDS
ORGANOBORONIC ACIDS
asymmetric synthesis
COUPLING REACTION
N-TOSYLARYLIMINES
boron
diene ligands
rhodium
ELECTRON-DEFICIENT OLEFINS
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Summary: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. The 1,4-adducts are produced in good yield and high enantioselectivity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200803230