Influence of the Solvent on the stereoselectivity of 1,3-Dipolar cycloaddition of Nitrile Oxides on Several 4-Substituted 2-Cyclopentenones-Reference-Cited by-同舟云学术

Influence of the Solvent on the stereoselectivity of 1,3-Dipolar cycloaddition of Nitrile Oxides on Several 4-Substituted 2-Cyclopentenones

Published:2003-03 Issue:3 Volume:2003 Page:126-127
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Adembri Giorgio¹,Paoli M. Laura¹,Sega Alessandro¹

Affiliation:

1. Dipartimento Farmaco Chimico Tecnologico, Università di Siena, Via Aldo Moro 53100 Siena

Abstract

The diastereofacial selectivity in 1,3-dipolar cycloadditions of 2,6-dichlorobenzonitrile oxide on 2-cyclopentenones 1–5 is strongly dependent on the solvent when an hydroxyl group is present at C(4) (1–2) while if this group is protected (3–4) or absent (5) the reaction is solvent independent.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/030823403103173453

Reference11 articles.

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4. Effect of solvent on the regioselectivity of cycloaddition of diazomethane to the thione group in adamantanethione

5. syn–anti-Isomerism in the cycloaddition of nitrile oxides to cis-3,4-dichlorocyclobutene

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