Synthesis 2013; 45(15): 2070-2078
DOI: 10.1055/s-0033-1339188
feature article
© Georg Thieme Verlag Stuttgart · New York

Ring-Expansion Reactions of Binaphthyl Azepines and Ferrocenophanes through Metal-Catalyzed [1,2]-Stevens Rearrangements

Steven Harthong
a   University of Geneva, Department of Organic Chemistry, Quai Ernest Ansermet 30, 1211 Geneva 4, Switzerland   Fax: +41(22)3793215   eMail: jerome.lacour@unige.ch
,
Renaud Bach
a   University of Geneva, Department of Organic Chemistry, Quai Ernest Ansermet 30, 1211 Geneva 4, Switzerland   Fax: +41(22)3793215   eMail: jerome.lacour@unige.ch
,
Céline Besnard
b   University of Geneva, Laboratory of Crystallography, Quai Ernest Ansermet 24, 1211 Geneva 4, Switzerland
,
Laure Guénée
b   University of Geneva, Laboratory of Crystallography, Quai Ernest Ansermet 24, 1211 Geneva 4, Switzerland
,
Jérôme Lacour*
a   University of Geneva, Department of Organic Chemistry, Quai Ernest Ansermet 30, 1211 Geneva 4, Switzerland   Fax: +41(22)3793215   eMail: jerome.lacour@unige.ch
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Publikationsverlauf

Received: 04. April 2013

Accepted after revision: 14. Mai 2013

Publikationsdatum:
25. Juni 2013 (online)


Abstract

Enantiopure binaphthyl azocines can be prepared in a single step via the direct copper-catalyzed reaction of binaphthyl azepines and α-diazo carbonyl reagents. The [1,2]-Stevens rearrangement is general (61–93% yields) and can be extended to [3]ferrocenophanes; similar reactivity in favor of the products of ring expansion is obtained with these ferrocene derivatives (80–96% yields).

Supporting Information