Three Carbons for Complexity! Recent Developments of Palladium-Catalyzed Reactions of Allenes

被引:107
|
作者
Lechel, Tilman [1 ,2 ]
Pfrengle, Fabian [1 ,3 ]
Reissig, Hans-Ulrich [1 ]
Zimmer, Reinhold [1 ]
机构
[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany
[2] LGC Ltd, D-14943 Luckenwalde, Germany
[3] Scripps Res Inst, Dept Physiol Chem, La Jolla, CA 92037 USA
关键词
allenes; carbocycles; cross-couplings; heterocycles; multicomponent reactions; palladium; COUPLING-CYCLIZATION REACTION; RING-EXPANSION REACTIONS; ANION CAPTURE PROCESSES; PALLADIUM(0)-CATALYZED TANDEM CYCLIZATION; HIGHLY STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC ALLYLIC ALKYLATION; FUNCTIONALLY-SUBSTITUTED ARYL; DIELS-ALDER REACTIONS; BETA-AMINO ALLENES; EFFICIENT SYNTHESIS;
D O I
10.1002/cctc.201200875
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The three carbon atoms of allene moieties allow unique transformations and rapid generation of complexity. Not surprisingly, allenes became extremely versatile building blocks in organic synthesis. Transition-metal-catalyzed reactions of these cumulene pi-systems have been particularly successful, and many applications in the synthesis of complex products have been reported. This review summarizes the palladium-catalyzed transformation of allenes published during the last decade. Many of the examples presented are impressive multicomponent processes or cascade reactions involving two or more steps leading to molecular complexity in simple one-pot operations. Consequently, several reactions have been developed with the goal of delivering new synthetic routes to natural products.
引用
收藏
页码:2100 / 2130
页数:31
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