Metal-Catalyzed [2+2+1] Cycloadditions of 1,3-Dienes, Allenes, and CO

UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
Mitchell Croatt, Assistant Professor (Creator)
The University of North Carolina at Greensboro (UNCG )
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Abstract: Step economy is a preeminent goal of synthesis.[1] It influences the length, efficiency, cost, time, separation, and environmental impact of a synthesis. Step economy is favored by the use of single, serial, or multicomponent reactions that proceed in one operation with a great increase in target revelant complexity. The design or discovery of such reactions is thus critical to extending the practical reach of organic synthesis. Toward this end, we have directed effort at the identification of new metal-catalyzed reactions, especially those which are forbidden or difficult to achieve in the absence of a catalyst. This program has thus far produced several new two-, three-, and four-component reactions, including [4+4],[2] [4+2],[3] [5+2],[4] [6+2],[5] [5+2+1],[6] [2+2+1],[7] [4+2+1],[7a] and [5+1+2+1][8] cycloadditions. Herein, we report the first examples of the [2+2+1] cycloaddition reaction of diene– allenes and CO and preliminary examples of acceleration of this process by Brønsted acids.

Additional Information

Angewandte Chemie (International Edition) 2006, 45, 2459-2462.
Language: English
Date: 2006
Allenes, Cycloaddition, Dienes, Pauson–Khand reaction, Rhodium

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