Reversal of regiochemistry in the synthesis of isoxazoles by nitrile oxide cycloadditions

Easton, Christopher J.; Hughes, C. Merrîcc; Tiekink, Edward R.T.; Lubin, Carolyn E.; Savage, G. Paul; Simpson, Gregory W.

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Reversal of regiochemistry in the synthesis of isoxazoles by nitrile oxide cycloadditions

Date

1994-05-23

Authors

Easton, Christopher J.

Abstract

The isoxazolines 2a, 2b and 8 obtained from nitrile oxide cycloadditions to cyclohex-2-enone 1a and its analogues 1b and 7 reacted with nickel peroxide to give the isoxazoles 3a, 3b and 9. In contrast, the corresponding 2-bromocyclohex-2-enones 4a, 4b and 10, prepared by bromination of the corresponding alkenes 1a, 1b and 7, underwent nitrile oxide cycloadditions to afford the regioisomeric isoxazoles 6a, 6b and 12, respectively.

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https://dspace-test.anu.edu.au/handle/1885/733726024

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DevOps Pure Testing

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Tetrahedron Letters

Type

Article

DOI

10.1016/S0040-4039(00)73248-5

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Reversal of regiochemistry in the synthesis of isoxazoles by nitrile oxide cycloadditions

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