An expeditious synthesis of 4-fluoropiperidines via aza-Prins cyclization

被引：34

作者：

Yadav, J. S. ^{[1
]}

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

Ramesh, K. ^{[1
]}

Kumar, G. G. K. S. Narayana ^{[1
]}

Gree, Rene ^{[2
]}

机构：

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

[2] Univ Rennes 1, Lab CPM, CNRS, UMR 6510, F-35042 Rennes, France

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 12期

关键词：

Aza-Prins cyclization; Tetrafluoroboric acid; Homoallylic amines; 4-Fluoropiperidines; RITTER REACTION SEQUENCE; CARBON BOND FORMATION; DIASTEREOSELECTIVE SYNTHESIS; MEDICINAL CHEMISTRY; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; VERSATILE REAGENT; DERIVATIVES; FLUORINE; HETEROCYCLES;

D O I：

10.1016/j.tetlet.2010.01.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of aldehydes with N-tosyl homoallylamine in the presence Of a Solution of tetrafluoroboric acid-diethyl ether complex in dichloromethane at ambient temperature gave the 4-fluoropiperidines in good yields and with high cis-selectivity. This aza-Prins-type cyclization has a wide scope and the use of HBF(4) OEt(2) makes this procedure simple, convenient, and cost-effective for the preparation of 4-fluoropiperidines. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1578 / 1581

页数：4

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