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

doi:10.1039/C0CC05161F

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Chemical Communications

Issue 20, 2011

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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 and Ben L. Feringa

Chem. Commun., 2011,47, 5843-5845

DOI: 10.1039/C0CC05161F
Received 24 Nov 2010, Accepted 01 Apr 2011
First published on the web 18 Apr 2011

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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.