Unprecedented Selectivity via Electronic Substrate Recognition in the 1,4-Addition to Cyclic Olefins Using a Chiral Disulfoxide Rhodium Catalyst

From zero to hero? Sulfoxides are generally not considered useful ligand entities in asymmetric metal catalysis. However, a chiral disulfoxide as a chelating ligand in the rhodium-catalyzed 1,4-addition of aryl boronic acids to cyclic, α,β-unsaturated ketones and esters gives impressive catalytic re...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2009-03, Vol.48 (15), p.2768-2771
Main Authors: Bürgi, Justus J, Mariz, Ronaldo, Gatti, Michele, Drinkel, Emma, Luan, Xinjun, Blumentritt, Sascha, Linden, Anthony, Dorta, Reto
Format: Article
Language:English
Subjects:
1,4‐additions
4-additions
asymmetric catalysis
Boronic Acids - chemistry
Catalysis
Cyclization
Cycloparaffins - chemistry
Esters - chemistry
homogeneous catalysis
Ketones - chemistry
Phosphines - chemistry
rhodium
Rhodium - chemistry
Stereoisomerism
sulfoxide ligands
Sulfoxides - chemistry
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Summary:From zero to hero? Sulfoxides are generally not considered useful ligand entities in asymmetric metal catalysis. However, a chiral disulfoxide as a chelating ligand in the rhodium-catalyzed 1,4-addition of aryl boronic acids to cyclic, α,β-unsaturated ketones and esters gives impressive catalytic results, thus opening the door to future applications of this new chiral ligand class.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200900429