4.4 Article

Radical cleavage of a β-hydroxy azide:: a reversal of regioselectivity in the oxidative fragmentation of hydroindoles

Journal

TETRAHEDRON LETTERS
Volume 41, Issue 24, Pages 4723-4727

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(00)00706-1

Keywords

regioselective oxidative fragmentation; hydroxy azide; keto nitrile

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Treatment of hydroindole 17 with PhI(OAc)(2)/I-2 leads to oxidative fragmentation of the beta-hydroxy azide moiety and results in the exclusive formation of keto nitrile 18 via radical cleavage of the lateral ring C-C bond. (C) 2000 Elsevier Science Ltd. All rights reserved.

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