Divergent Outcomes of Carbene Transfer Reactions from Dirhodium- and Copper-Based Catalysts Separately or in Combination

Divergent catalysis: The use of copper and rhodium catalysts separately or in combination directs reactions between vinyldiazoacetates 1 and cinnamaldehydes 2 from formal [4+3] cycloaddition (epoxidation followed by Cope rearrangement), to intramolecular cyclopropanation, to Mukaiyama‐aldol reaction...

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Veröffentlicht in:	Angewandte Chemie International Edition 2011-11, Vol.50 (47), p.11152-11155
Hauptverfasser:	Xu, Xinfang, Hu, Wen-Hao, Zavalij, Peter Y., Doyle, Michael P.
Format:	Artikel
Sprache:	eng
Schlagworte:	[4+3]-cycloaddition Acrolein - analogs & derivatives Acrolein - chemistry Catalysis copper Copper - chemistry Crystallography, X-Ray Cycloaddition Reaction intramolecular cyclopropanation Methane - analogs & derivatives Methane - chemistry Molecular Conformation Mukaiyama-aldol reaction rhodium Rhodium - chemistry
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Beschreibung
Zusammenfassung:	Divergent catalysis: The use of copper and rhodium catalysts separately or in combination directs reactions between vinyldiazoacetates 1 and cinnamaldehydes 2 from formal [4+3] cycloaddition (epoxidation followed by Cope rearrangement), to intramolecular cyclopropanation, to Mukaiyama‐aldol reactions. The reactions proceed selectively and in high yield.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201105557