Gold(I)-Catalyzed Tandem Cyclization-Selective Migration Reaction of 1,3-Dien-5-ynes: Regioselective Synthesis of Highly Substituted Benzenes

被引：45
|
作者：
Garcia-Garcia, Patricia [1 ]
Martinez, Alberto [1 ]
Sanjuan, Ana M. [1 ]
Fernandez-Rodriguez, Manuel A. [1 ]
Sanz, Roberto [1 ]
机构：
[1] Univ Burgos, Fac Ciencias, Dept Quim, Area Quim Organ, Burgos 09001, Spain
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 18期
关键词：
AROMATIC ENYNES; GOLD CATALYSIS; SKELETAL REARRANGEMENT; 1,2-INDOLE MIGRATIONS; 1,2-ALKYL MIGRATION; CYCLOISOMERIZATION; NAPHTHALENES; DERIVATIVES; EFFICIENT; 3-SILYLOXY-1,5-ENYNES;
D O I：
10.1021/ol202129n
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Highly substituted benzene derivatives have been easily prepared in a regioselective way from readily available 1,3-hexadien-5-ynes through a gold(I)-catalyzed tandem reaction. The process involves an initial cyclization followed by a selective Wagner-Meerwein shift in which the migration preference seems to be determined by the ability to stabilize a positive charge.
引用
收藏
页码：4970 / 4973
页数：4
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