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

[1] Reaction of ynolate anions derived from silylketenes with electrophiles: A facile preparation of silyl ynol ethers and functionalized silylketenes [J].

Akai, S ;

Kitagaki, S ;

Naka, T ;

Yamamoto, K ;

Tsuzuki, Y ;

Matsumoto, K ;

Kita, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (14) :1705-1709

[2] Amination of bis(trimethylsilyl)-1,2-bisketene with secondary amines: Formation of aminodihydrofuranones [J].

Allen, AD ;

Huang, WW ;

Moore, PA ;

Far, AR ;

Tidwell, TT .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) :5676-5679

[3]

[Anonymous], [No title captured]

[4] Reactions of (trialkylsilyl)vinylketenes with lithium ynolates: A new benzannulation strategy [J].

Austin, WF ;

Zhang, YJ ;

Danheiser, RL .

ORGANIC LETTERS, 2005, 7 (18) :3905-3908

[5] Hetero [4+2] cycloadditions of (trialkylsilyl)vinylketenes.: Synthesis of α,β-unsaturated δ-valerolactones and -lactams [J].

Bennett, DM ;

Okamoto, I ;

Danheiser, RL .

ORGANIC LETTERS, 1999, 1 (04) :641-644

[6] Determination of the overlapping pKa values of resorcinol using UV-visible spectroscopy and DFT methods [J].

Blanco, SE ;

Almandoz, MC ;

Ferretti, FH .

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2005, 61 (1-2) :93-102

[7] WOLFF REARRANGEMENT OF (1-DIAZO-2-OXOALKYL) SILANES [J].

BRUCKMANN, R ;

SCHNEIDER, K ;

MAAS, G .

TETRAHEDRON, 1989, 45 (17) :5517-5530

[8] SYNTHONS FOR THE PARENT VINYL CARBENE COMPLEX IN THE BENZANNULATION REACTION [J].

CHAMBERLIN, S ;

WULFF, WD .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3047-3054

[9] Formation of medium-ring heterocycles by diene and enyne metathesis [J].

Chattopadhyay, Shital K. ;

Karmakar, Swastik ;

Biswas, Titas ;

Majumdar, K. C. ;

Rahaman, H. ;

Roy, B. .

TETRAHEDRON, 2007, 63 (19) :3919-3952

[10] [2+2], [4+1], and [4+2] cycloaddition reactions of silylated bisketenes [J].

Colomvakos, JD ;

Egle, I ;

Ma, JH ;

Pole, DL ;

Tidwell, TT ;

Warkentin, J .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9522-9527

← 1 2 3 4 5 6 →