Chemoenzymatic Synthesis and Application of Bicyclo[2.2.2]octadiene Ligands: Increased Efficiency in Rhodium-Catalyzed Asymmetric Conjugate Additions by Electronic Tuning

Chemoenzymatic Synthesis and Application of Bicyclo[2.2.2]octadiene Ligands: Increased Efficiency in Rhodium-Catalyzed Asymmetric Conjugate Additions by Electronic Tuning

On your bi(cycle)ke! A series of 1,4‐dimethyl bicyclic [2.2.2] diene ligands with tunable substitution at the bridge positions was accessed using a lipase resolution and a high yielding six step sequence (see scheme). The bridgehead methyl groups improve efficiency allowing less aryl boronic acid to...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2010-04, Vol.49 (15), p.2750-2754
Hauptverfasser: Luo, Yunfei, Carnell, Andrew J
Format: Artikel
Sprache:eng
Schlagworte:
asymmetric catalysis
Boronic Acids - chemistry
Bridged Bicyclo Compounds - chemistry
Catalysis
chemoenzymatic synthesis
chiral dienes
conjugate addition
Electrons
Ligands
Lipase - metabolism
rhodium
Rhodium - chemistry
Stereoisomerism
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Beschreibung
Zusammenfassung:On your bi(cycle)ke! A series of 1,4‐dimethyl bicyclic [2.2.2] diene ligands with tunable substitution at the bridge positions was accessed using a lipase resolution and a high yielding six step sequence (see scheme). The bridgehead methyl groups improve efficiency allowing less aryl boronic acid to be used in the title reaction.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200907033