Highly Diastereoselective Conjugate Addition to Alkylidene Bis(Sulfoxides): Asymmetric Synthesis of (+)-erythro-Roccellic Acid

Authors

  • Franck Brebion,

    1. Laboratoire de Chimie Organique, UMR 7611 CNRS, Case 229, Université Pierre et Marie Curie, 4, place Jussieu, 75252 Paris Cedex 05, France, Fax: (+33) 1-4427-7360
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  • Bénédicte Delouvrié,

    1. Laboratoire de Chimie Organique, UMR 7611 CNRS, Case 229, Université Pierre et Marie Curie, 4, place Jussieu, 75252 Paris Cedex 05, France, Fax: (+33) 1-4427-7360
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  • Francisco Nájera Dr.,

    1. Laboratoire de Chimie Organique, UMR 7611 CNRS, Case 229, Université Pierre et Marie Curie, 4, place Jussieu, 75252 Paris Cedex 05, France, Fax: (+33) 1-4427-7360
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  • Louis Fensterbank Dr.,

    1. Laboratoire de Chimie Organique, UMR 7611 CNRS, Case 229, Université Pierre et Marie Curie, 4, place Jussieu, 75252 Paris Cedex 05, France, Fax: (+33) 1-4427-7360
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  • Max Malacria Prof. Dr.,

    1. Laboratoire de Chimie Organique, UMR 7611 CNRS, Case 229, Université Pierre et Marie Curie, 4, place Jussieu, 75252 Paris Cedex 05, France, Fax: (+33) 1-4427-7360
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  • Jacqueline Vaissermann Dr.

    1. Laboratoire de Chimie Inorganique et Matériaux Moléculaires, UMR 7071 CNRS, Université Pierre et Marie Curie, 4, place Jussieu, 75252 Paris Cedex 05, France
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  • We thank the Ministère de la Recherche for PhD grants to F.B. and B.D., and the CNRS for a Poste Rouge to F.N. as well as for their financial support. We also thank Carine Taboret for technical assistance, Patrick Herson (UPMC) for the X-ray analysis of 1 c, and Dr. Bernold Hasenknopf (UPMC) for helpful discussions. We are very grateful to Professor N. P. Argade (NCL Pune, India) for providing us with NMR spectra of erythro-roccellic acid.

Abstract

original image

Faciale Stereokontrolle ist möglich bei Additionen von Nucleophilen (Nu) an Alkylidenbis(sulfoxide): In Gegenwart geeigneter Lewis-Säuren (LA) erfolgt die Reaktion über Chelatkomplexe (B), was eine andere Konfiguration im Produkt zur Folge hat. Dies wurde zur Lösung eines Problems bei der ersten Totalsynthese von (+)-erythro-Roccellsäure genutzt.

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