Regioselective Gold-Catalyzed Allylative Ring Opening of 1,4-Epoxy-1,4-dihydronaphthalenes

被引：25
|
作者：
Sawama, Yoshinari [1 ]
Kawamoto, Koichi [1 ]
Satake, Hiroyuki [1 ]
Krause, Norbert [2 ]
Kita, Yasuyuki [1 ]
机构：
[1] Ritsumeikan Univ, Coll Pharmaceut Sci, Kusatsu, Shiga 5258577, Japan
[2] Dortmund Univ Technol, D-44227 Dortmund, Germany
来源：
SYNLETT | 2010年 / 14期
基金：
日本学术振兴会;
关键词：
allylation; ring opening; regioselectivity; naphthalene; gold catalyst; OXABICYCLIC ALKENES; HETEROBICYCLIC ALKENES; BICYCLIC OLEFINS; PHOSPHINE LIGAND; GRIGNARD; REAGENTS; ENANTIOSELECTIVITY; DERIVATIVES; HALIDES;
D O I：
10.1055/s-0030-1258528
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In the presence of a gold catalyst, the ring opening of 1,4-epoxy-1,4-dihydronaphthalenes with allyltrimethylsilane affords allylnaphthalenes in high yield. For unsymmetrical substrates, high regioselectivity is observed in many cases. This reaction might proceed via tricyclic tetrahydrofuran intermediates which are formed stereoselectively.
引用
收藏
页码：2151 / 2155
页数：5
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