First Epoxidation Reaction of Carbonyl Compounds via Ferrocenyl Sulfur Ylides

Stéphanie Minière; Vincent Reboul; Ramón Gómez Arrayás; Patrick Metzner; Juan Carlos Carretero

doi:10.1055/s-2003-41445

SPECIALTOPIC

First Epoxidation Reaction of Carbonyl Compounds via Ferrocenyl Sulfur Ylides

Stéphanie Minière^a, Vincent Reboul^a, Ramón Gómez Arrayás^b, Patrick Metzner*^a, Juan Carlos Carretero^b
^a Laboratoire de Chimie Moléculaire et Thio-organique (UMR CNRS 6507), ENSICAEN-Université, 6, boulevard du Maréchal Juin, 14050 Caen, France
^b Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, 28049, Madrid, Spain
Fax: +33(231)452877; e-Mail: Metzner@ismra.fr;

Abstract

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Abstract

Epoxidation reactions of carbonyl compounds (aldehydes and a ketone) mediated by sulfanyl ferrocenes have been successfully achieved in a one-pot reaction, under mild conditions. This reaction implies intermediary formation of a sulfonium salt (a ferrocenyl one was observed for the first time by ¹H NMR) and then an ylide. The diastereoselectivity of the formation of stilbene oxide was unusual: the effect of steric hindrance and aromatic nature of the sulfide substituents have been evidenced. A catalytic asymmetric example with a planar chiral ferrocene is described.

Key words

sulfur - ylides - epoxidations - aldehydes - ferrocene - stereoselectivity

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References

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