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: [email protected]
,
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: [email protected]
,
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: [email protected]
,
Gianluigi Broggini*
a  Dipartimento di Scienza e Alta Tecnologia, Università dell’Insubria, Via Valleggio 11, 22100, Como, Italy   Email: [email protected]
› Author Affiliations
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.
Further Information

Publication History

Received: 31 August 2017

Accepted after revision: 04 October 2017

Publication Date:
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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