Literature DB >> 28608622

SN 2 Reactions at Tertiary Carbon Centers in Epoxides.

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

Abstract

Described herein is a novel concept for SN 2 reactions at tertiary carbon centers in epoxides without activation of the leaving group. Quantum chemical calculations show why SN 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.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

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

Year:  2017        PMID： 28608622     DOI： 10.1002/anie.201702882

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  4 in total

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Journal:  Angew Chem Int Ed Engl       Date:  2022-05-11       Impact factor: 16.823

2.  Bioinspired Asymmetric Total Synthesis of Emeriones A-C.

Authors:  Sven Jänner; Daniel Isak; Yuli Li; Kendall N Houk; Aubry K Miller
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-28       Impact factor: 16.823

3.  Titanocene(III)-Catalyzed Precision Deuteration of Epoxides.

Authors:  Dina Schwarz G Henriques; Elena Rojo-Wiechel; Sven Klare; Regine Mika; Sebastian Höthker; Jonathan H Schacht; Niklas Schmickler; Andreas Gansäuer
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-21       Impact factor: 16.823

4.  Markovnikov alcohols via epoxide hydroboration by molecular alkali metal catalysts.

Authors:  Guoqi Zhang; Haisu Zeng; Shengping Zheng; Michelle C Neary; Pavel A Dub
Journal:  iScience       Date:  2022-09-12
  4 in total

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