Unusual biaryl torsional strain promotes reactivity in Cu-catalyzed Sommelet–Hauser rearrangement

A Cu-catalyzed Sommelet–Hauser dearomatization of dihydrophenanthridine and diazo compounds is reported for the synthesis of spiro-indolines. A spiro-structure with adjacent quaternary and tertiary carbon centers was constructed in one step as a single isomer. Increasing steric hindrance by introduc...

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Autores principales: Pan, Chongqing, Guo, Wenjing, Gu, Zhenhua
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6050577/
https://www.ncbi.nlm.nih.gov/pubmed/30079198
http://dx.doi.org/10.1039/c8sc01657g
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author Pan, Chongqing
Guo, Wenjing
Gu, Zhenhua
author_facet Pan, Chongqing
Guo, Wenjing
Gu, Zhenhua
author_sort Pan, Chongqing
collection PubMed
description A Cu-catalyzed Sommelet–Hauser dearomatization of dihydrophenanthridine and diazo compounds is reported for the synthesis of spiro-indolines. A spiro-structure with adjacent quaternary and tertiary carbon centers was constructed in one step as a single isomer. Increasing steric hindrance by introducing ortho-substituents dramatically improved substrate reactivity in this transformation.
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spelling pubmed-60505772018-08-03 Unusual biaryl torsional strain promotes reactivity in Cu-catalyzed Sommelet–Hauser rearrangement Pan, Chongqing Guo, Wenjing Gu, Zhenhua Chem Sci Chemistry A Cu-catalyzed Sommelet–Hauser dearomatization of dihydrophenanthridine and diazo compounds is reported for the synthesis of spiro-indolines. A spiro-structure with adjacent quaternary and tertiary carbon centers was constructed in one step as a single isomer. Increasing steric hindrance by introducing ortho-substituents dramatically improved substrate reactivity in this transformation. Royal Society of Chemistry 2018-06-14 /pmc/articles/PMC6050577/ /pubmed/30079198 http://dx.doi.org/10.1039/c8sc01657g Text en This journal is © The Royal Society of Chemistry 2018 https://creativecommons.org/licenses/by-nc/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Pan, Chongqing
Guo, Wenjing
Gu, Zhenhua
Unusual biaryl torsional strain promotes reactivity in Cu-catalyzed Sommelet–Hauser rearrangement
title Unusual biaryl torsional strain promotes reactivity in Cu-catalyzed Sommelet–Hauser rearrangement
title_full Unusual biaryl torsional strain promotes reactivity in Cu-catalyzed Sommelet–Hauser rearrangement
title_fullStr Unusual biaryl torsional strain promotes reactivity in Cu-catalyzed Sommelet–Hauser rearrangement
title_full_unstemmed Unusual biaryl torsional strain promotes reactivity in Cu-catalyzed Sommelet–Hauser rearrangement
title_short Unusual biaryl torsional strain promotes reactivity in Cu-catalyzed Sommelet–Hauser rearrangement
title_sort unusual biaryl torsional strain promotes reactivity in cu-catalyzed sommelet–hauser rearrangement
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6050577/
https://www.ncbi.nlm.nih.gov/pubmed/30079198
http://dx.doi.org/10.1039/c8sc01657g
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AT guowenjing unusualbiaryltorsionalstrainpromotesreactivityincucatalyzedsommelethauserrearrangement
AT guzhenhua unusualbiaryltorsionalstrainpromotesreactivityincucatalyzedsommelethauserrearrangement

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