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

Harthong, Steven; Bach, Renaud; Besnard, Céline; Guenee, Laure; Lacour, Jérôme

doi:10.1055/s-0033-1339188

Scientific article

English

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

ContributorsHarthong, Steven; Bach, Renaud; Besnard, Céline; Guenee, Laure; Lacour, Jérôme

Published inSynthesis, vol. 45, no. 15, p. 2070-2078

Publication date2013

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).

Keywords

azepine
azocine
diazo ester
ferrocenophane
[1,2]-Stevens rearrangement

Affiliation

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

HARTHONG, Steven et al. Ring-Expansion Reactions of Binaphthyl Azepines and Ferrocenophanes through Metal-Catalyzed [1,2]-Stevens Rearrangements. In: Synthesis, 2013, vol. 45, n° 15, p. 2070–2078. doi: 10.1055/s-0033-1339188

Article (Published version)

Identifiers

PID : unige:28961
DOI : 10.1055/s-0033-1339188

ISSN of the journal0039-7881

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

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