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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 02期

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

页码：265 / 269

页数：5

共 93 条

[1] Cobalt-catalyzed cyclotrimerization of alkynes: The answer to the puzzle of parallel reaction pathways [J].