Enantioselective Synthesis of Bicyclo[2.2.2]octenones Using a Copper-Mediated Oxidative Dearomatization/[4 + 2] Dimerization Cascade

Enantioselective Synthesis of Bicyclo[2.2.2]octenones Using a Copper-Mediated Oxidative Dearomatization/[4 + 2] Dimerization Cascade

An enantioselective approach to bicyclo[2.2.2]octenone structures utilizing a copper-mediated asymmetric oxidative dearomatization/[4 + 2] dimerization cascade is described. The total synthesis and absolute stereochemistry reassignment of (+)-aquaticol has been achieved using the methodology.

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Veröffentlicht in:Journal of the American Chemical Society 2008-03, Vol.130 (9), p.2738-2739
Hauptverfasser: Dong, Suwei, Zhu, Jianglong, Porco, John A
Format: Artikel
Sprache:eng
Schlagworte:
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Copper - chemistry
Cyclization
Cyclooctanes - chemical synthesis
Cyclooctanes - chemistry
Dimerization
Molecular Conformation
Organometallic Compounds - chemistry
Oxidation-Reduction
Stereoisomerism
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Zusammenfassung:An enantioselective approach to bicyclo[2.2.2]octenone structures utilizing a copper-mediated asymmetric oxidative dearomatization/[4 + 2] dimerization cascade is described. The total synthesis and absolute stereochemistry reassignment of (+)-aquaticol has been achieved using the methodology.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja711018z