Synlett 2018; 29(04): 503-508
DOI: 10.1055/s-0036-1590939
letter
© Georg Thieme Verlag Stuttgart · New York

Selective 7-endo-Cyclization of 3-Aza-5-alkenols through Oxidative Pd(II)-Catalyzed Olefin Oxyarylation

Silvia Gazzola
a   Dipartimento di Scienza e Alta Tecnologia, Università dell’Insubria, Via Valleggio 11, 22100, Como, Italy   eMail: gianluigi.broggini@uninsubria.it
,
Egle M. Beccalli
b   DISFARM, Sezione di Chimica Generale e Organica ‘A. Marchesini’ Università degli Studi di Milano, Via Venezian 21, 20133 Milano, Italy
,
Tea Borelli
a   Dipartimento di Scienza e Alta Tecnologia, Università dell’Insubria, Via Valleggio 11, 22100, Como, Italy   eMail: gianluigi.broggini@uninsubria.it
,
Carlo Castellano
c   Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy
,
Daria Diamante
a   Dipartimento di Scienza e Alta Tecnologia, Università dell’Insubria, Via Valleggio 11, 22100, Como, Italy   eMail: gianluigi.broggini@uninsubria.it
,
Gianluigi Broggini*
a   Dipartimento di Scienza e Alta Tecnologia, Università dell’Insubria, Via Valleggio 11, 22100, Como, Italy   eMail: gianluigi.broggini@uninsubria.it
› Institutsangaben
Università degli Studi dell’Insubria and Università degli Studi di ­Milano are acknowledged for financial support. Support through CMST COST Action, CA15106 (CHAOS) is also gratefully acknowledged.
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Publikationsverlauf

Received: 31. August 2017

Accepted after revision: 04. Oktober 2017

Publikationsdatum:
08. November 2017 (online)


Abstract

3-Aza-5-alkenols undergo selective 7-endo-trig cyclization when treated with a catalytic Pd(II) species, CuCl2 and ArSnBu3 giving 7-aryl-substituted oxazepanes. The intramolecular alkoxylation occurs with formation of a seven-membered ring only when associated with an arylating step. Otherwise, 6-exo-trig reactions, providing morpholine derivatives, were observed.

Supporting Information

 
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