Issue 46, 2012
From the journal:

Organic & Biomolecular Chemistry

Highly regioselective nitrile oxide dipolar cycloadditions with ortho-nitrophenyl alkynes†

Melissa L. McIntosh,a   Michael R. Naffziger,a   Bradley O. Ashburn,a   Lev N. Zakharovb  and  Rich G. Carter*a  

* Corresponding authors

a Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, Oregon 97331, USA
E-mail: rich.carter@oregonstate.edu
Fax: +1 541-737-2062
Tel: +1 541-737-9486

b Director of the X-ray Crystallographic Facility of the Departments of Chemistry at Oregon State University and the University of Oregon, USA
E-mail: lev@uoregon.edu

Abstract

The dipolar cycloadditions of ortho-nitrophenyl alkynes with aryl nitrile oxides has been demonstrated. A range of substituents are tolerated on the alkyne. These reactions proceed with excellent levels of regioselectivity. Subsequent functionalization of the isoxazole scaffold has been demonstrated.

Graphical abstract: Highly regioselective nitrile oxide dipolar cycloadditions with ortho-nitrophenyl alkynes

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Article information

DOI
https://doi.org/10.1039/C2OB26267C
Article type
Paper
Submitted
04 Jul 2012
Accepted
04 Oct 2012
First published
23 Oct 2012

Org. Biomol. Chem., 2012,10, 9204-9213

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Highly regioselective nitrile oxide dipolar cycloadditions with ortho-nitrophenyl alkynes

M. L. McIntosh, M. R. Naffziger, B. O. Ashburn, L. N. Zakharov and R. G. Carter, Org. Biomol. Chem., 2012, 10, 9204 DOI: 10.1039/C2OB26267C

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