Synthesis of Highly Functionalized Cyclohexenone Rings: Rhodium-Catalyzed 1,3-Acyloxy Migration and Subsequent [5+1] Cycloaddition

Lead Rh‐ole: Highly substituted cyclohexenones were prepared from cyclopropyl‐substituted propargyl esters by using a [{Rh(CO)2Cl}2] catalyst. This metal catalyst promoted the 1,3‐acyloxy migration of propargyl esters and a subsequent [5+1] cycloaddition of the resulting allenylcyclopropanes in the...

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Veröffentlicht in:	Angewandte Chemie (International ed.) 2011-02, Vol.50 (6), p.1346-1349
Hauptverfasser:	Shu, Dongxu, Li, Xiaoxun, Zhang, Min, Robichaux, Patrick J, Tang, Weiping
Format:	Artikel
Sprache:	eng
Schlagworte:	carbocycle Catalysis cycloaddition Cyclohexenes - chemical synthesis Cyclohexenes - chemistry Cyclopropanes - chemical synthesis Cyclopropanes - chemistry rhodium Rhodium - chemistry ring expansion Stereoisomerism synthetic methods
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Beschreibung
Zusammenfassung:	Lead Rh‐ole: Highly substituted cyclohexenones were prepared from cyclopropyl‐substituted propargyl esters by using a [{Rh(CO)2Cl}2] catalyst. This metal catalyst promoted the 1,3‐acyloxy migration of propargyl esters and a subsequent [5+1] cycloaddition of the resulting allenylcyclopropanes in the presence of CO with high regioselectivity.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201006881