SN 2 Reactions at Tertiary Carbon Centers in Epoxides

Yong-Qiang Zhang; Christina Poppel; Anastasia Panfilova; Fabian Bohle; Stefan Grimme; Andreas Gansäuer

doi:10.1002/anie.201702882

S_N 2 Reactions at Tertiary Carbon Centers in Epoxides

Angew Chem Int Ed Engl. 2017 Aug 7;56(33):9719-9722. doi: 10.1002/anie.201702882. Epub 2017 Jul 18.

Authors

Yong-Qiang Zhang¹, Christina Poppel¹, Anastasia Panfilova¹, Fabian Bohle², Stefan Grimme², Andreas Gansäuer¹

Affiliations

¹ Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard Domagk Strasse 1, 53121, Bonn, Germany.
² Mulliken Center for Theoretical Chemistry, Institut für Physikalische Chemie und Theoretische Chemie, Universität Bonn, Beringstrasse 4, 53115, Bonn, Germany.

PMID: 28608622
DOI: 10.1002/anie.201702882

Abstract

Described herein is a novel concept for S_N 2 reactions at tertiary carbon centers in epoxides without activation of the leaving group. Quantum chemical calculations show why S_N 2 reactions at tertiary carbon centers are proceeding in these systems. The reaction allows flexible synthesis of 1,3-diol building blocks for natural product synthesis with excellent control of the relative and absolute configurations.

Keywords: epoxides; hydrides; nucleophilic substitution; polyols; reaction mechanisms.

Publication types

Research Support, Non-U.S. Gov't