Heteropoly acid catalyzed synthesis of 8-methyl-2-aryl/alkyl-3-oxabicyclo[3.3.1]non-7-ene derivatives through (3,5)-oxonium-ene reaction

被引：10

作者：

Anjibabu, R. ^{[1
,2
]}

Sau, Samaresh ^{[3
]}

Reddy, B. Jagan Mohan ^{[2
]}

Banerjee, Rajkumar ^{[3
]}

Reddy, B. V. Subba ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Technol, Nat Prod Chem, Hyderabad 500007, Andhra Pradesh, India

[2] Adikavi Nannaya Univ, Dept Organ Chem, Rajahmundry 533105, India

[3] CSIR Indian Inst Chem Technol, Biomat Grp, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 52期

关键词：

Heteropoly acid; Oxonium-ene reaction; Aldehydes; Alkenols; Oxabicyclo[3.3.1]non-7-ene; SOLID ACIDS; CYCLIZATION;

D O I：

10.1016/j.tetlet.2013.10.103

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of aldehydes undergo a smooth coupling with (4-methylcyclohex-3-en-1-yl)methanol in the presence of 2 mol % of phosphomolybdic acid in dichloromethane to afford 3-oxabicyclo[3.3.1]non-7-ene in good yields through 3,5-oxonium-ene cyclization under mild conditions. The use of inexpensive, nontoxic, and readily available heteropoly acid catalyst makes this method simple, convenient, and environmental-friendly. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：7160 / 7163

页数：4

共 32 条

[1] Highly efficient one-pot three-component Mannich reaction in water catalyzed by heteropoly acids [J].

Azizi, N ;

Torkiyan, L ;

Saidi, MR .

ORGANIC LETTERS, 2006, 8 (10) :2079-2082

[2]

Chauzov V. A., 1997, RUSS J ORG CHEM+, V67, P160

[3]

Chauzov V. A., 2006, RUSS J ORG CHEM+, V1996, P66

[4] Highly efficient chemical kinetic resolution of bishomoallylic alcohols:: Synthesis of (R)-sulcatol [J].

Chen, SL ;

Hu, QY ;

Loh, TP .

ORGANIC LETTERS, 2004, 6 (19) :3365-3367

[5] Solid acids for green chemistry [J].

Clark, JH .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (09) :791-797

[6] Estrogen receptor null mice: What have we learned and where will they lead us? [J].

Couse, JF ;

Korach, KS .

ENDOCRINE REVIEWS, 1999, 20 (03) :358-417

[7]

Gramenitskaya V. N., 1975, J ORG CHEM USSR, V11, P4654

[8]

Hamamoto H, 2002, CHEM-EUR J, V8, P5377, DOI 10.1002/1521-3765(20021202)8:23<5377::AID-CHEM5377>3.0.CO

[9]

2-H

[10] Structure-activity relationships and sub-type selectivity in an oxabicyclic estrogen receptor α/β agonist scaffold [J].

Hamann, LG ;

Meyer, JH ;

Ruppar, DA ;

Marschke, KB ;

Lopez, FJ ;

Allegretto, EA ;

Karanewsky, DS .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (05) :1463-1466

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