Synthesis 2012; 44(10): 1511-1514
DOI: 10.1055/s-0031-1290821
special topic
© Georg Thieme Verlag Stuttgart · New York

Regio- and Stereoselective Copper-Catalyzed Ring Opening of Dihetero­bicyclic Alkenes with Grignard Reagents

Stefano Crotti
Dipartimento di Scienze Farmaceutiche, Sede di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy
,
Valeria Di Bussolo
Dipartimento di Scienze Farmaceutiche, Sede di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy
,
Mauro Pineschi*
Dipartimento di Scienze Farmaceutiche, Sede di Chimica Bioorganica e Biofarmacia, Università di Pisa, Via Bonanno 33, 56126 Pisa, Italy
› Author Affiliations
Further Information

Publication History

Received: 01 March 2012

Accepted after revision: 09 March 2012

Publication Date:
11 April 2012 (online)

Abstract

The ring opening of bicyclic hydrazines and bicyclic oxazines with organomagnesium reagents under the influence of copper catalysts allows functionalized cyclopentene and cyclohexene derivatives to be obtained. Whereas complete anti-stereoselective ring opening occurred in all cases, the regioselective outcome turned out to be highly dependent on the reaction conditions used.

 
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