Gold-Catalyzed Allenamide [2+2+2]-Cyclotrimerization

被引:18
作者
Hernandez-Diaz, Cristina [1 ,2 ]
Rubio, Eduardo [1 ,2 ]
Gonzalez, Jose M. [1 ,2 ]
机构
[1] Univ Oviedo, Dept Quim Organ & Inorgan, C Julian Claveria 8, Oviedo 33006, Spain
[2] Univ Oviedo, Inst Univ Quim Organometal Enr Moles, C Julian Claveria 8, Oviedo 33006, Spain
关键词
Allenamides; C-C coupling; Cyclotrimerization; Gold; Homogeneous catalysis; Selectivity; ENANTIOSELECTIVE 2+2+2 CYCLOADDITION; N-ALLENYL AMIDES; INTERMOLECULAR CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; SUBSTITUTED ALLENES; ENE-ALLENES; CYCLOTRIMERIZATION; INDOLES; CONSTRUCTION;
D O I
10.1002/ejoc.201501364
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A protocol involving a gold(I)-catalyzed reaction to elaborate cyclic frames by selective trimerization reactions of N-allenylsulfonamides is reported. Efficiency in the formation of the target [2+2+2] products depends on the concentration of the reagents, the nature of the ancillary ligand on the gold catalyst, and, to a significant extent, on the selection of a low reaction temperature. This singular catalytic allene cycloaddition gives adducts in high isolated yields. In addition to representing a new gold-catalyzed reaction, the reported allenamide cyclotrimerization offers a significant extension to the scant number of allenes that have effectively entered this cyclization mode by use of other metal-catalyzed reactions. Upon aromatization of the assembled adducts, the overall reaction matches the outcome of related and widely investigated alkyne trimerization reactions.
引用
收藏
页码:265 / 269
页数:5
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