Ruthenium-catalyzed [2+2] cycloaddition reactions of a 2-oxa-3-azabicyclo[2.2.1]hept-5-ene with unsymmetrical alkynes-Reference-Cited by-同舟云学术

Ruthenium-catalyzed [2+2] cycloaddition reactions of a 2-oxa-3-azabicyclo[2.2.1]hept-5-ene with unsymmetrical alkynes

Published:2011-12 Issue:12 Volume:89 Page:1494-1505
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Durham Robin¹,Mandel Jérémie²,Blanchard Nicolas²,Tam William¹

Affiliation:

1. Guelph–Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, ON N1G 2W1, Canada.

2. Université de Haute-Alsace, École Nationale Supérieure de Chimie de Mulhouse, Laboratoire de Chimie Organique et Bioorganique EA4566, 3 rue A. Werner, 68093 Mulhouse CEDEX, France.

Abstract

Ruthenium-catalyzed [2+2] cycloaddition reactions of a 2-oxa-3-azabicyclo[2.2.1]hept-5-ene with unsymmetrical alkynes were investigated. Yields of up to 90% were obtained though regioselectivity was modest. Select cycloadducts could be separated and used to access a highly functionalized [3.2.0] bicyclic structure through reductive cleavage of the N–O bond. These ring-opened products displayed a chemical exchange phenomenon in 1D carbon NMR and required characterization by 2D NMR techniques.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v11-135

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