Chelation-control in the formal [3+3] cyclization of 1,3-bis-(silyloxy)-1,3-butadienes with 1-hydroxy-5-silyloxy-hex-4-en-3-ones. One-pot synthesis of 3-aryl-3,4-dihydroisocoumarins

被引：7

作者：

Ullah, Ihsan ^{[1
,2
]}

Sher, Muhammad ^{[1
,2
,3
]}

Khera, Rasheed Ahmad ^{[1
]}

Ali, Asad ^{[1
,2
]}

Ibad, Muhammad Farooq ^{[1
]}

Villinger, Alexander ^{[1
]}

Fischer, Christine ^{[2
]}

Langer, Peter ^{[1
,2
]}

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

[3] Allama Iqbal Open Univ, Dept Chem, Islamabad, Pakistan

来源：

TETRAHEDRON | 2010年 / 66卷 / 10期

关键词：

Arenes; Cyclizations; Isocoumarins; Regioselectivity; Silyl enol ethers; HYDRANGEAE-DULCIS-FOLIUM; THUNBERGINOL-G; 3-O-GLUCOSIDE; 1,3-BIS(SILYL ENOL ETHERS); BIOACTIVE FUNCTIONS; (-)-HYDRANGENOL 4-O-GLUCOSIDE; ANTIMICROBIAL PRINCIPLES; VAR; THUNBERGII; SILYL ETHERS; PHYLLODULCIN; MACROPHYLLA;

D O I：

10.1016/j.tet.2010.01.019

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The [3+3] cyclization of 1,3-bis(silyloxy)-1,3-butadienes with 1-hydroxy-5-silyloxy-hex-4-en-3-ones resulted in the one-pot formation of 3-aryl-3,4-dihydroisocoumarins. The reactions proceeded by regioselective cyclization to give 6-(2-aryl-2-chloroethyl)salicylates, which underwent a silica gel-mediated lactonization. The cyclizations of protected 1-amino-5-silyloxy-hex-4-en-3-ones proved to be not regioselective. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1874 / 1884

页数：11

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