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
› Author Affiliations
Further Information

Publication History

Received: 04 April 2013

Accepted after revision: 14 May 2013

Publication Date:
25 June 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

 
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