Stereoselective synthesis of syn and anti 1,2-hydroxyalkyl moieties by Cu-catalyzed asymmetric allylic alkylation†,10.1039/C0CC05161F

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Stereoselective synthesis of syn and anti 1,2-hydroxyalkyl moieties by Cu-catalyzed asymmetric allylic alkylation†

Martín Fañanás-Mastral,Bjorn ter Horst,Adriaan J. Minnaard,Ben L. Feringa

Chemical Communications Pub Date : 04/18/2011 00:00:00 , DOI:10.1039/C0CC05161F

Abstract

A stereoselective synthesis of 1,2-hydroxyalkyl moieties is described herein. These valuable building blocks are obtained with complete regiocontrol and excellent stereocontrol both for the syn or the anti products, by choosing the appropriate enantiomer of the ligand in a copper-catalyzed asymmetric allylic alkylation of δ-alkoxy-substituted allyl bromides.