A benzannulation strategy for the synthesis of phenols and heteroaromatic compounds based on the reaction of (trialkylsilyl)vinylketenes with lithium ynolates

被引：35

作者：

Austin, Wesley F. ^{[1
]}

Zhang, Yongjun ^{[1
]}

Danheiser, Rick L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

TETRAHEDRON | 2008年 / 64卷 / 05期

关键词：

(Trialkylsilyl)vinylketenes; benzannulation; ynolates; electrocyclic ring closure;

D O I：

10.1016/j.tet.2007.10.113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(Trialkylsilyl)vinylketenes react with lithium ynolates to generate 3-(oxido)dienylketenes, which undergo rapid 6 pi-electrocyclization. The ultimate products of this benzannulation are highly substituted resorcinol monosilyl ethers, which are formed via a [1,3] carbon to oxygen silyl group shift. Further transformations of the benzannulation products are described providing efficient access to ortho-benzoquinones and benzofuran, benzoxepine, and benzoxocine ring systems. (c) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：915 / 925

页数：11

相关论文

共 56 条

[31]

KLEIN J, 1971, ISRAEL J CHEM, V9, P177

[32] YNOL SILYL ETHERS VIA O-SILYLATION OF ESTER-DERIVED YNOLATE ANIONS [J].

KOWALSKI, CJ ;

LAL, GS ;

HAQUE, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7127-7128

[33] Novel highly regioselective VO(acac)2/TBHP mediated oxidation of o-alkenyl phenols to o-hydroxybenzyl ketones [J].

Lattanzi, A ;

Senatore, A ;

Massa, A ;

Scettri, A .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09) :3691-3694

[34] (Trialkylsilyl)vinylketenes: Synthesis and application as diene components in Diels-Alder cycloadditions [J].

Loebach, JL ;

Bennett, DM ;

Danheiser, RL .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8380-8389

[35] The reaction of (trialkylsilyl)vinylketenes with carbenoid reagents: A new [4+1] annulation route to cyclopentenones [J].

Loebach, JL ;

Bennett, DM ;

Danheiser, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (37) :9690-9691

[36] PREPARATION OF 1-ARYL-2-SILOXYALKYNES FROM SILYLATED ALPHA-DIAZO CARBONYL-COMPOUNDS [J].

MAAS, G ;

BRUCKMANN, R .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (15) :2801-2802

[37]

MAGNUS P, 1978, NOUV J CHIM, V2, P555

[38] Chemoselective cyclizations of divinyl ketones to cyclohexenones mediated by Lewis acid and base [J].

Magomedov, NA ;

Ruggiero, PL ;

Tang, YC .

ORGANIC LETTERS, 2004, 6 (19) :3373-3375

[39] Remarkably facile hexatriene electrocyclizations as a route to functionalized cyclohexenones via ring expansion of cyclobutenones [J].

Magomedov, NA ;

Ruggiero, PL ;

Tang, YC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) :1624-1625

[40] Synthesis and reactivity of silyl vinylketenes: A formal interrupted Dotz benzannulation with unexpected silyl migration [J].

Moser, WH ;

Sun, LD ;

Huffman, JC .

ORGANIC LETTERS, 2001, 3 (21) :3389-3391

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