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

Authors
Wipf, P Mareska, DA
Citation
P. Wipf et Da. Mareska, Radical cleavage of a beta-hydroxy azide: a reversal of regioselectivity in the oxidative fragmentation of hydroindoles, TETRAHEDR L, 41(24), 2000, pp. 4723-4727
Citations number
21
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
24
Year of publication
2000
Pages
4723 - 4727
Database
ISI
SICI code
0040-4039(20000615)41:24<4723:RCOABA>2.0.ZU;2-2
Abstract
Treatment of hydroindole 17 with PhI(OAc)(2)/I-2 leads to oxidative fragmen tation of the beta-hydroxy azide moiety and results in the exclusive format ion of keto nitrile 18 via radical cleavage of the lateral ring C-C bond. ( C) 2000 Elsevier Science Ltd. All rights reserved.