General, Highly Selective Synthesis of 1,3- and 1,4-Difunctionalized Building Blocks by Regiodivergent Epoxide Opening

Nico Funken; Felix Mühlhaus; Andreas Gansäuer

doi:10.1002/anie.201606064

General, Highly Selective Synthesis of 1,3- and 1,4-Difunctionalized Building Blocks by Regiodivergent Epoxide Opening

Angew Chem Int Ed Engl. 2016 Sep 19;55(39):12030-4. doi: 10.1002/anie.201606064. Epub 2016 Sep 7.

Authors

Nico Funken¹, Felix Mühlhaus¹, Andreas Gansäuer²

Affiliations

¹ Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Str. 1, 53121, Bonn, Germany.
² Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Str. 1, 53121, Bonn, Germany. andreas.gansaeuer@uni-bonn.de.

PMID: 27600090
DOI: 10.1002/anie.201606064

Abstract

We describe a regiodivergent epoxide opening (REO) featuring a catalyst-controlled synthesis of enantiomerically and diastereomerically highly enriched or pure syn- and anti- 1,3- and 1,4-difunctionalized building blocks from a common epoxide precursor. The REO is attractive for natural product synthesis and as a branching reaction for diversity-oriented synthesis with epoxides.

Keywords: electron transfer; epoxides; polyols; radicals; titanium.