Chiral sulfur derivatives in the allylation of acyl hydrazones: C2-symmetric bis-sulfinamides as enhanced chiral organic promoters.

Inmaculada Fernández; Ana Alcudia; Beatrice Gori; Victoria Valdivia; Rocío Recio; María Victoria García; Noureddine Khiar

doi:10.1039/C0OB00078G

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Chiral sulfur derivatives in the allylation of acyl hydrazones: C₂-symmetric bis-sulfinamides as enhanced chiral organic promoters.†

Inmaculada Fernández,*^a Ana Alcudia,^a Beatrice Gori,^a Victoria Valdivia,^b Rocío Recio,^a María Victoria García^a and Noureddine Khiar*^b

Author affiliations

* Corresponding authors

^a Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad de Sevilla, Spain
E-mail: inmaff@us.es
Fax: (+) 34 95 455 67 37
Tel: (+)34 95 455 59 93

^b Instituto de Investigaciones Químicas, C.S.I.C-Universidad de Sevilla, c/Américo Vespucio, s/n., Isla de la Cartuja, , Spain
E-mail: khiar@iiq.csic.es
Fax: (+) 34 95 446 05 65
Tel: (+) 34 95 448 95 59

Abstract

Monosulfinamides and C₂-symmetric bis-sulfinamides are convenient neutral chiral promoters in the allylation of acyl hydrazones, the nature of the spacer and the substituent at the sulfinyl sulfur are key elements for the enantioselectivity of the process.

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Supplementary files

Full experimental procedures, characterization data and copies of NMR spectra for all compounds PDF (1510K)

Article information

DOI: https://doi.org/10.1039/C0OB00078G
Article type: Paper
Submitted: 04 May 2010
Accepted: 28 Jun 2010
First published: 06 Aug 2010

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Org. Biomol. Chem., 2010,8, 4388-4393

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Chiral sulfur derivatives in the allylation of acyl hydrazones: C₂-symmetric bis-sulfinamides as enhanced chiral organic promoters.

I. Fernández, A. Alcudia, B. Gori, V. Valdivia, R. Recio, M. V. García and N. Khiar, Org. Biomol. Chem., 2010, 8, 4388 DOI: 10.1039/C0OB00078G

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Organic & Biomolecular Chemistry