Asymmetric Synthesis of 2,3‐Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o‐Quinone Methides

A highly enantio‐ and diastereoselective [4+1] annulation between in situ generated ammonium ylides and o‐quinone methides for the synthesis of a variety of 2,3‐dihydrobenzofurans has been developed. The key factors controlling the reactivity and stereoselectivity were systematically investigated by...

Descripción completa

Detalles Bibliográficos
Autores principales: Meisinger, Nicole, Roiser, Lukas, Monkowius, Uwe, Himmelsbach, Markus, Robiette, Raphaël, Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5419452/
https://www.ncbi.nlm.nih.gov/pubmed/28165173
http://dx.doi.org/10.1002/chem.201700171
_version_ 1783234225611210752
author Meisinger, Nicole
Roiser, Lukas
Monkowius, Uwe
Himmelsbach, Markus
Robiette, Raphaël
Waser, Mario
author_facet Meisinger, Nicole
Roiser, Lukas
Monkowius, Uwe
Himmelsbach, Markus
Robiette, Raphaël
Waser, Mario
author_sort Meisinger, Nicole
collection PubMed
description A highly enantio‐ and diastereoselective [4+1] annulation between in situ generated ammonium ylides and o‐quinone methides for the synthesis of a variety of 2,3‐dihydrobenzofurans has been developed. The key factors controlling the reactivity and stereoselectivity were systematically investigated by experimental and computational means and the energy profiles obtained provide a deeper insight into the mechanistic details of this reaction.
format Online
Article
Text
id pubmed-5419452
institution National Center for Biotechnology Information
language English
publishDate 2017
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-54194522017-05-05 Asymmetric Synthesis of 2,3‐Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o‐Quinone Methides Meisinger, Nicole Roiser, Lukas Monkowius, Uwe Himmelsbach, Markus Robiette, Raphaël Waser, Mario Chemistry Full Papers A highly enantio‐ and diastereoselective [4+1] annulation between in situ generated ammonium ylides and o‐quinone methides for the synthesis of a variety of 2,3‐dihydrobenzofurans has been developed. The key factors controlling the reactivity and stereoselectivity were systematically investigated by experimental and computational means and the energy profiles obtained provide a deeper insight into the mechanistic details of this reaction. John Wiley and Sons Inc. 2017-03-27 2017-04-11 /pmc/articles/PMC5419452/ /pubmed/28165173 http://dx.doi.org/10.1002/chem.201700171 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Meisinger, Nicole
Roiser, Lukas
Monkowius, Uwe
Himmelsbach, Markus
Robiette, Raphaël
Waser, Mario
Asymmetric Synthesis of 2,3‐Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o‐Quinone Methides
title Asymmetric Synthesis of 2,3‐Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o‐Quinone Methides
title_full Asymmetric Synthesis of 2,3‐Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o‐Quinone Methides
title_fullStr Asymmetric Synthesis of 2,3‐Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o‐Quinone Methides
title_full_unstemmed Asymmetric Synthesis of 2,3‐Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o‐Quinone Methides
title_short Asymmetric Synthesis of 2,3‐Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o‐Quinone Methides
title_sort asymmetric synthesis of 2,3‐dihydrobenzofurans by a [4+1] annulation between ammonium ylides and in situ generated o‐quinone methides
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5419452/
https://www.ncbi.nlm.nih.gov/pubmed/28165173
http://dx.doi.org/10.1002/chem.201700171
work_keys_str_mv AT meisingernicole asymmetricsynthesisof23dihydrobenzofuransbya41annulationbetweenammoniumylidesandinsitugeneratedoquinonemethides
AT roiserlukas asymmetricsynthesisof23dihydrobenzofuransbya41annulationbetweenammoniumylidesandinsitugeneratedoquinonemethides
AT monkowiusuwe asymmetricsynthesisof23dihydrobenzofuransbya41annulationbetweenammoniumylidesandinsitugeneratedoquinonemethides
AT himmelsbachmarkus asymmetricsynthesisof23dihydrobenzofuransbya41annulationbetweenammoniumylidesandinsitugeneratedoquinonemethides
AT robietteraphael asymmetricsynthesisof23dihydrobenzofuransbya41annulationbetweenammoniumylidesandinsitugeneratedoquinonemethides
AT wasermario asymmetricsynthesisof23dihydrobenzofuransbya41annulationbetweenammoniumylidesandinsitugeneratedoquinonemethides

Ejemplares similares