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

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

Chemical communications (Cambridge, England) (2011-04-20)
Martín Fañanás-Mastral, Bjorn ter Horst, Adriaan J Minnaard, Ben L Feringa
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.

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Sigma-Aldrich
Allile bromuro, ReagentPlus®, 99%, contains ≤1000 ppm propylene oxide as stabilizer
Sigma-Aldrich
Allile bromuro, reagent grade, 97%, contains ≤1000 ppm propylene oxide as stabilizer