Addition of Bis-sulfinyl Anions to Ketones: Stereoselective Synthesis of Allylic Alcohols through Evans-Mislow Rearrangement Based Domino Reactions

Franck Brebion; Francisco Nàjera; Bénédicte Delouvrié; Emmanuel Lacôte; Louis Fensterbank; Max Malacria

doi:10.1055/s-2007-966070

PAPER

Addition of Bis-sulfinyl Anions to Ketones: Stereoselective Synthesis of Allylic Alcohols through Evans-Mislow Rearrangement Based Domino Reactions

Franck Brebion, Francisco Nàjera, Bénédicte Delouvrié, Emmanuel Lacôte*, Louis Fensterbank*, Max Malacria*
Université Pierre et Marie Curie-Paris 6, Laboratoire de chimie organique (UMR CNRS 7611), Institut de chimie moléculaire (FR 2769), 4 place Jussieu, C. 229, 75005 Paris, France
Fax: +33(1)44277360; e-Mail: lacote@ccr.jussieu.fr; e-Mail: louis.fensterbank@upmc.fr; e-Mail: max.malacria@upmc.fr;

Abstract

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Abstract

Enantiopure cyclic allylic alcohols were obtained from cyclic ketones and bis-sulfoxides through a domino reaction mixing anionic and concerted elementary steps. Total transfer of chirality was achieved, presumably through cooperative effects of both sulfoxides units. Depending on the ring size, both sulfinyl groups could be converted, giving C ₂-symmetric bis-allylic alcohols.

Key words

alkenation - carbanion - pericyclic reaction - sulfoxide - sulfur

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References

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