Preparation of a C2-Symmetric Binol-Derived Diol and Its Application in the Catalytic Enantioselective and Catalyst-Controlled Diastereoselective Allylboration of Aldehydes

Vivek Rauniyar; Dennis G. Hall

doi:10.1055/s-2007-983832

PSP

Preparation of a C ₂-Symmetric Binol-Derived Diol and Its Application in the Catalytic Enantioselective and Catalyst-Controlled Diastereoselective Allylboration of Aldehydes

Vivek Rauniyar, Dennis G. Hall*
Department of Chemistry, University of Alberta, Edmonton, AB, T6G 2G2, Canada
Fax: +1(780)4928231; e-Mail: dennis.hall@ualberta.ca;

Abstract

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Abstract

A novel C ₂-symmetric Binol-derived diol is described. It is readily applicable towards combined acid catalysis for the asymmetric allylboration of aldehydes to provide homoallylic alcohols in high enantioselectivities, and dictates the diastereoselectivity in the reaction of an achiral allylboronate with chiral aldehydes.

Keywords

allylboration - Brønsted acid - enantioselective catalysis - chiral diol - propionate units

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References

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Preparation of a C 2-Symmetric Binol-Derived Diol and Its Application in the Catalytic Enantioselective and Catalyst-Controlled Diastereoselective Allylboration of Aldehydes

Preparation of a C ₂-Symmetric Binol-Derived Diol and Its Application in the Catalytic Enantioselective and Catalyst-Controlled Diastereoselective Allylboration of Aldehydes