An Expeditious Enantioselective Synthesis of Methyl trans-Chrysanthemate

Alain  Krief; Willy  Dumont; Diane  Baillieul

doi:10.1055/s-2002-34388

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Synthesis 2002(14): 2019-2022
DOI: 10.1055/s-2002-34388

PAPER

An Expeditious Enantioselective Synthesis of Methyl trans-Chrysanthemate

Alain Krief*^a, Willy Dumont^a, Diane Baillieul^b
^a Laboratoire de Chimie Organique de Synthèse, Département de Chimie, Facultés Universitaires Notre-Dame de la Paix, 61 rue de Bruxelles, 5000 Namur, Belgium
Fax: +32(81)724539; e-Mail: alain.krief@fundp.ac.be;
^b Fonds pour la Recherche Scientifique dans l’Industrie et l’Agriculture (F.R.I.A.), 5 rue d’Egmont, Bruxelles, 1000, Belgium

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Publication History

Received 21 June 2002
Publication Date:
26 September 2002 (online)

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Abstract

Methyl trans-chrysanthemate has been prepared in few steps from isopropylidenediphenylsulfurane and methyl (E)-3-(3,3-dimethyloxiran-2-yl)prop-2-enoate. The latter was obtained from methyl 4-oxobutenoate or 3-methylbut-2-en-1-ol. The Sharpless catalytic epoxidation reaction allows an asymmetric version of this transformation.

Key words

sulfur ylides - cyclopropanation - asymmetric induction - Sharpless epoxidation

References

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8

Work is in progress to understand the scope and limitation of this reaction.