Tetrahedron Letters, volume 51, issue 12, pages 1578-1581

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

J. S. Yadav ¹

B.V.Subba Reddy ¹

Ramesh K ¹

G G K S Narayana Kumar ¹

R. Grée ²

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Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500-007, India |

Université de Rennes 1, Laboratoire CPM, CNRS UMR 6510, Avenue du Général Leclerc, 35042 Rennes Cedex, France |

Publication type: Journal Article

Publication date: 2010-03-01

Elsevier

Journal: Tetrahedron Letters

scimago Q3

wos Q3

SJR: 0.323

CiteScore: 3.5

Impact factor: 1.5

ISSN: 00404039, 18733581

DOI: 10.1016/j.tetlet.2010.01.059

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Organic Chemistry

Drug Discovery

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Abstract

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 HBF4·OEt2 makes this procedure simple, convenient, and cost-effective for the preparation of 4-fluoropiperidines.

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Publisher

Elsevier

Journal

Tetrahedron Letters

scimago Q3

wos Q3

SJR

0.323

CiteScore

3.5

Impact factor

1.5

ISSN

00404039 (Print)

18733581 (Electronic)

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

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