Cargando…
Enantioselective Pallada‐Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes
Asymmetric pallada‐electrocatalyzed C−H olefinations were achieved through the synergistic cooperation with transient directing groups. The electrochemical, atroposelective C−H activations were realized with high position‐, diastereo‐, and enantio‐control under mild reaction conditions to obtain hig...
Autores principales: | , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497116/ https://www.ncbi.nlm.nih.gov/pubmed/32243685 http://dx.doi.org/10.1002/anie.202003826 |
_version_ | 1783583247552217088 |
---|---|
author | Dhawa, Uttam Tian, Cong Wdowik, Tomasz Oliveira, João C. A. Hao, Jiping Ackermann, Lutz |
author_facet | Dhawa, Uttam Tian, Cong Wdowik, Tomasz Oliveira, João C. A. Hao, Jiping Ackermann, Lutz |
author_sort | Dhawa, Uttam |
collection | PubMed |
description | Asymmetric pallada‐electrocatalyzed C−H olefinations were achieved through the synergistic cooperation with transient directing groups. The electrochemical, atroposelective C−H activations were realized with high position‐, diastereo‐, and enantio‐control under mild reaction conditions to obtain highly enantiomerically‐enriched biaryls and fluorinated N−C axially chiral scaffolds. Our strategy provided expedient access to, among others, novel chiral BINOLs, dicarboxylic acids and helicenes of value to asymmetric catalysis. Mechanistic studies by experiments and computation provided key insights into the catalyst's mode of action. |
format | Online Article Text |
id | pubmed-7497116 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-74971162020-09-25 Enantioselective Pallada‐Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes Dhawa, Uttam Tian, Cong Wdowik, Tomasz Oliveira, João C. A. Hao, Jiping Ackermann, Lutz Angew Chem Int Ed Engl Research Articles Asymmetric pallada‐electrocatalyzed C−H olefinations were achieved through the synergistic cooperation with transient directing groups. The electrochemical, atroposelective C−H activations were realized with high position‐, diastereo‐, and enantio‐control under mild reaction conditions to obtain highly enantiomerically‐enriched biaryls and fluorinated N−C axially chiral scaffolds. Our strategy provided expedient access to, among others, novel chiral BINOLs, dicarboxylic acids and helicenes of value to asymmetric catalysis. Mechanistic studies by experiments and computation provided key insights into the catalyst's mode of action. John Wiley and Sons Inc. 2020-06-05 2020-08-03 /pmc/articles/PMC7497116/ /pubmed/32243685 http://dx.doi.org/10.1002/anie.202003826 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Research Articles Dhawa, Uttam Tian, Cong Wdowik, Tomasz Oliveira, João C. A. Hao, Jiping Ackermann, Lutz Enantioselective Pallada‐Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes |
title | Enantioselective Pallada‐Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes |
title_full | Enantioselective Pallada‐Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes |
title_fullStr | Enantioselective Pallada‐Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes |
title_full_unstemmed | Enantioselective Pallada‐Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes |
title_short | Enantioselective Pallada‐Electrocatalyzed C−H Activation by Transient Directing Groups: Expedient Access to Helicenes |
title_sort | enantioselective pallada‐electrocatalyzed c−h activation by transient directing groups: expedient access to helicenes |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497116/ https://www.ncbi.nlm.nih.gov/pubmed/32243685 http://dx.doi.org/10.1002/anie.202003826 |
work_keys_str_mv | AT dhawauttam enantioselectivepalladaelectrocatalyzedchactivationbytransientdirectinggroupsexpedientaccesstohelicenes AT tiancong enantioselectivepalladaelectrocatalyzedchactivationbytransientdirectinggroupsexpedientaccesstohelicenes AT wdowiktomasz enantioselectivepalladaelectrocatalyzedchactivationbytransientdirectinggroupsexpedientaccesstohelicenes AT oliveirajoaoca enantioselectivepalladaelectrocatalyzedchactivationbytransientdirectinggroupsexpedientaccesstohelicenes AT haojiping enantioselectivepalladaelectrocatalyzedchactivationbytransientdirectinggroupsexpedientaccesstohelicenes AT ackermannlutz enantioselectivepalladaelectrocatalyzedchactivationbytransientdirectinggroupsexpedientaccesstohelicenes |