Tetrahedron Letters, volume 34, issue 14, pages 2315-2318

Substituent control in the synthesis of azetidines and pyrrolidines by N-tosyl-oxiraneethylamines base-mediated cyclization.

Jean Moulines ¹

Jean Paul Bats ¹

Patrick Hautefaye ¹

Alain Nührich ²

Anne Marie Lamidey ¹

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Laboratoire de Chimie Appliquée, Université de Bordeaux I, 351 Cours de la Libération, 33405 Talence France |

Laboratoire de Chmie Thérapeutique, Université de bordeaux II, 3 Place de la Victoire, 33076 Bordeaux France |

Publication type: Journal Article

Publication date: 1993-04-01

Elsevier

Journal: Tetrahedron Letters

scimago Q3

wos Q3

SJR: 0.323

CiteScore: 3.5

Impact factor: 1.5

ISSN: 00404039, 18733581

DOI: 10.1016/s0040-4039(00)77602-7

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

N-tosyl-oxiraneethylamines undergo cyclization upon treatment with aqueous sodium hydroxide to afford either N-tosyl-azetidinemethanols or N-tosyl-pyrrolidin-3-ols in high yields. The change in regioselectivity of this cyclization process is quite dependent on the location of a pentamethylene substitution in the chain connecting the nitrogen with the oxirane ring.

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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)

Substituent control in the synthesis of azetidines and pyrrolidines by N-tosyl-oxiraneethylamines base-mediated cyclization.

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