C2-symmetric bissulfoxides as organocatalysts in the allylation of benzoyl hydrazones: spacer and concentration effects

Inmaculada Fernández; Victoria Valdivia; Manuel Pernía Leal; Noureddine Khiar

doi:10.1021/ol070729d

C2-symmetric bissulfoxides as organocatalysts in the allylation of benzoyl hydrazones: spacer and concentration effects

Org Lett. 2007 May 24;9(11):2215-8. doi: 10.1021/ol070729d. Epub 2007 May 3.

Authors

Inmaculada Fernández¹, Victoria Valdivia, Manuel Pernía Leal, Noureddine Khiar

Affiliation

¹ Departamento de Química OrgAnica y Farmacéutica, Facultad de Farmacia, Universidad de Sevilla, 41012 Sevilla, Spain. inmaff@us.es

PMID: 17474752
DOI: 10.1021/ol070729d

Abstract

A comparative study on the allylation of a benzoyl hydrazone with allyl trichlorosilane using monosulfoxides, methylene-bridged C2-symmetric bissulfoxides, and ethylene-bridged C2-symmetric bissulfoxides shows that the enantioselectivity of the process is highly dependent on the spacer between the two sulfinyl sulfurs and the concentration of the reaction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Hydrazones / chemistry*
Molecular Structure
Sulfoxides / chemistry*

Substances

Hydrazones
Sulfoxides