Issue 20, 2011
From the journal:

Chemical Communications

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

Martín Fañanás-Mastral,a   Bjorn ter Horst,a   Adriaan J. Minnaarda  and  Ben L. Feringa*a  

* Corresponding authors

a Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands
E-mail: b.l.feringa@rug.nl
Fax: +31 50 363 4296
Tel: +31 50 363 4235

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.

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

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Article information

DOI
https://doi.org/10.1039/C0CC05161F
Article type
Communication
Submitted
24 Nov 2010
Accepted
01 Apr 2011
First published
18 Apr 2011

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

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

M. Fañanás-Mastral, B. ter Horst, A. J. Minnaard and B. L. Feringa, Chem. Commun., 2011, 47, 5843 DOI: 10.1039/C0CC05161F

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