One-pot synthesis of functionalized carbacycles by formal [3+3] cyclizations of 1,3-bis(silyl enol ethers) with 1,3-dielectrophiles

被引：134

作者：

Feist, Holger

Langer, Peter

机构：

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

[2] Univ Rostock, Leiniz Inst Katal eV, D-18059 Rostock, Germany

来源：

SYNTHESIS-STUTTGART | 2007年 / 03期

关键词：

arenes; cyclization; one-pot reaction; salicylic acid; silylenol ethers;

D O I：

10.1055/s-2006-958958

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lewis acid mediated [3+3] cyclizations of 1,3-bis(silyl enol ethers) with 1,3-dielectrophiles, such as 1,1,3,3-tetramethoxypropane, 3-silyloxy-2-en-1-ones and 1,1-diacylcyclopropanes, provide an efficient approach to a variety of functionalized arenes (such as salicylates and phenols) and other six-membered carbacyclic products.

引用

收藏

页码：327 / 347

页数：21

相关论文

共 45 条

[31] Synthesis of 6-(perfluoroalkyl)salicylates by [3+3] cyclization of 1,3-bis(silyl enol ethers) with 3-ethoxy-1-(perfluoroalkyl)prop-2-en-1-ones [J].

Lubbe, Mathias ;

Mamat, Constantin ;

Fischer, Christine ;

Langer, Peter .

TETRAHEDRON, 2007, 63 (02) :413-418

[32] Regioselective synthesis of 2-acetyl- and 2-alkoxycarbonyl-3-(trifluoromethyl)phenols by [3+3] cyclization of 1,3-bis-silyl enol ethers with 4-ethoxy- and 4-silyloxy-1,1,1-trifluoroalk-3-en-2-ones [J].

Mamat, C ;

Pundt, T ;

Schmidt, A ;

Langer, P .

TETRAHEDRON LETTERS, 2006, 47 (13) :2183-2185

[33] Synthesis of functionalized arylalkyl and diaryl ethers by [3+3] cyclization of 3-alkoxy- and 3-aryloxy-1-siloxy-1,3-butadienes with 3-(silyloxy)alk-2-en-1-ones [J].

Mross, Gerson ;

Langer, Peter .

TETRAHEDRON LETTERS, 2006, 47 (48) :8519-8521

[34] Synthesis of chromanes by sequential '[3+3]-cyclization/Williamson' reactions of 1,3-bis(trimethylsilyloxy)-7-chlorohepta-1,3-dienes [J].

Nguyen, Van Thi Hong ;

Appel, Bettina ;

Langer, Peter .

TETRAHEDRON, 2006, 62 (33) :7674-7686

[35] Synthesis of functionalized benzopyrans by sequential [3+3]-cyclization-Williamson reactions of 1.3-bis(trimethylsilyloxy)-7-chlorohepta-1,3-dienes [J].

Nguyen, VH ;

Langer, P .

TETRAHEDRON LETTERS, 2005, 46 (05) :815-817

[36] Synthesis of 3-alkyl- and 3-chloroalkyl-2-hydroxybenzoates based on [3+3] cyclizations of 4-alkyl- and 4-chloroalkyl-1,3-bis(trimethylsilyloxy)buta-1,3-dienes [J].

Nguyen, VTH ;

Bellur, E ;

Appel, B ;

Langer, P .

SYNTHESIS-STUTTGART, 2006, 7 (07) :1103-1110

[37] Synthesis of 2,5-dihydrobenzo[b]oxepines and 5,6-dihydro-2H-benzo[b]oxocines based on a '[3+3] cyclization-olefin-metathesis' strategy [J].

Nguyen, VTH ;

Bellur, E ;

Langer, P .

TETRAHEDRON LETTERS, 2006, 47 (01) :113-116

[38] Synthesis of dibenzo[b,d]pyran-6-ones based on a '[3+3] cyclization-Suzuki cross-coupling' strategy [J].

Nguyen, VTH ;

Langer, P .

TETRAHEDRON LETTERS, 2005, 46 (06) :1013-1015

[39]

REIM S, UNPUB

[40] Synthesis of fluorenones based on a '[3+3] cyclization/Suzuki cross-coupling/Friedel-Crafts acylation' strategy [J].

Reim, Stefanie ;

Lau, Matthias ;

Langer, Peter .

TETRAHEDRON LETTERS, 2006, 47 (38) :6903-6905

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