Synthesis 2005(14): 2449-2452  
DOI: 10.1055/s-2005-872089
© Georg Thieme Verlag Stuttgart · New York

Highly Diastereoselective Michael Additions onto Dienyl Bis-Sulfoxides

Franck Brebion, Jean Philippe Goddard, Louis Fensterbank*, Max Malacria*
Université Pierre et Marie Curie, UMR CNRS 7611, Institut de chimie moleculaire, FR 2769, case 229, 4 place Jussieu, 75252 Paris cedex 05, France
e-Mail: [email protected]; e-Mail: [email protected];
Further Information

Publication History

Received 14 March 2005
Publication Date:
20 July 2005 (online)


An optimized procedure for the preparation of (S S,S S)-bis(p-tolylsulfinyl)methane (4) is reported. Condensation of the lithium salt of 4 onto cinnamaldehyde furnished bis-sulfoxide dienyl derivative 5, a remarkable 1,4-Michael acceptor that can lead in a highly dia­stereoselective manner to vinylcyclopropyl adducts. In a chelating mode of reactivity using a methylcopper reagent, a complete reversal of stereoselectivity is observed giving an enantiopure β,γ-unsaturated methyl ester intermediate that is used in the synthesis of cryptophycin.


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