Barbier allylation-Prins reaction of PEG-bound aldehydes-soluble polymer-supported synthesis of 2,4,6-trisubstituted tetrahydropyrans

被引：19

作者：

Kumar, HMS ^{[1
]}

Qazi, NA

Shafi, S

Kumar, VN

Krishna, AD

Yadav, JS

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India

[2] Reg Res Lab, Jammu 180001, India

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 42期

关键词：

PEG; Barbier allylation; prins cyclization; tetrahydropyran;

D O I：

10.1016/j.tetlet.2005.08.070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

PEG-bound aldehydes undergo zinc-mediated Barbier allylation to form homoallylic alcohols, which on further reaction with various aldehydes in the presence of BF3 center dot Et2O through a Prins cyclization afford 4-hydroxytetrahydropyrans and 4-fluorotetrahydropyrans. (c) 2005 Published by Elsevier Ltd.

引用

页码：7205 / 7207

页数：3

共 7 条

[1]

Balkenhohl F, 1996, ANGEW CHEM INT EDIT, V35, P2289

[2] Solid-phase organic reactions: A review of the recent literature [J].

Hermkens, PHH ;

Ottenheijm, HCJ ;

Rees, D .

TETRAHEDRON, 1996, 52 (13) :4527-4554

[3]

Nicolaou K.C., 1996, Classics in Total Synthesis

[4] Polymer-supported (salen)Mn catalysts for asymmetric epoxidation: A comparison between soluble and insoluble matrices [J].

Reger, TS ;

Janda, KD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (29) :6929-6934

[5]

Wentworth P, 1999, CHEM COMMUN, P1917

[6] Highly stereoselective prins cyclization of silylmethyl-substituted cyclopropyl carbinols to 2,4,6-trisubstituted tetrahydropyrans [J].

Yadav, VK ;

Kumar, NV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) :8652-8653

[7] Highly effective synthesis of 4-halo-tetrahydropyrans via a highly diastereoselective in situ prins-type cyclization reaction [J].

Yang, J ;

Viswanathan, GS ;

Li, CJ .

TETRAHEDRON LETTERS, 1999, 40 (09) :1627-1630

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