Investigation of the scope of a [3+2] cycloaddition approach to isoxazole boronic esters

The [3+2] cycloaddition reaction of nitrile oxides and alkynylboronates provides direct access to a wide variety of isoxazole boronic esters. Specifically, this technique has been employed to generate trisubstituted isoxazole 4-boronates and disubstituted isoxazoles where the boronic ester moiety ca...

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Bibliographic Details
Published in:Tetrahedron 2005-07, Vol.61 (28), p.6707-6714
Main Authors: Moore, Jane E., Davies, Mark W., Goodenough, Katharine M., Wybrow, Robert A.J., York, Mark, Johnson, Christopher N., Harrity, Joseph P.A.
Format: Article
Language:English
Subjects:
Boronic esters
Cycloadditions
Isoxazoles
Regioselective
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Summary:The [3+2] cycloaddition reaction of nitrile oxides and alkynylboronates provides direct access to a wide variety of isoxazole boronic esters. Specifically, this technique has been employed to generate trisubstituted isoxazole 4-boronates and disubstituted isoxazoles where the boronic ester moiety can be installed at C-4 or C-5 with high levels of regiocontrol. The application of this methodology in the synthesis of non-steroidal antiinflammatory agents is also described. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.05.015