A Chiral Thiourea as a Template for Enantioselective Intramolecular [2 + 2] Photocycloaddition Reactions

[Image: see text] A chiral (1R,2R)-diaminocyclohexane-derived bisthiourea was found to exhibit a significant asymmetric induction in the intramolecular [2 + 2] photocycloaddition of 2,3-dihydropyridone-5-carboxylates. Under optimized conditions, the reaction was performed with visible light employin...

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Autores principales: Mayr, Florian, Brimioulle, Richard, Bach, Thorsten
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4994062/
https://www.ncbi.nlm.nih.gov/pubmed/27258626
http://dx.doi.org/10.1021/acs.joc.6b01039
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author Mayr, Florian
Brimioulle, Richard
Bach, Thorsten
author_facet Mayr, Florian
Brimioulle, Richard
Bach, Thorsten
author_sort Mayr, Florian
collection PubMed
description [Image: see text] A chiral (1R,2R)-diaminocyclohexane-derived bisthiourea was found to exhibit a significant asymmetric induction in the intramolecular [2 + 2] photocycloaddition of 2,3-dihydropyridone-5-carboxylates. Under optimized conditions, the reaction was performed with visible light employing 10 mol % of thioxanthone as triplet sensitizer. Due to the different electronic properties of its carbonyl oxygen atoms, a directed binding of the substrate to the template is possible, which in turn enables an efficient enantioface differentiation.
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spelling pubmed-49940622016-08-24 A Chiral Thiourea as a Template for Enantioselective Intramolecular [2 + 2] Photocycloaddition Reactions Mayr, Florian Brimioulle, Richard Bach, Thorsten J Org Chem [Image: see text] A chiral (1R,2R)-diaminocyclohexane-derived bisthiourea was found to exhibit a significant asymmetric induction in the intramolecular [2 + 2] photocycloaddition of 2,3-dihydropyridone-5-carboxylates. Under optimized conditions, the reaction was performed with visible light employing 10 mol % of thioxanthone as triplet sensitizer. Due to the different electronic properties of its carbonyl oxygen atoms, a directed binding of the substrate to the template is possible, which in turn enables an efficient enantioface differentiation. American Chemical Society 2016-06-03 2016-08-19 /pmc/articles/PMC4994062/ /pubmed/27258626 http://dx.doi.org/10.1021/acs.joc.6b01039 Text en Copyright © 2016 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Mayr, Florian
Brimioulle, Richard
Bach, Thorsten
A Chiral Thiourea as a Template for Enantioselective Intramolecular [2 + 2] Photocycloaddition Reactions
title A Chiral Thiourea as a Template for Enantioselective Intramolecular [2 + 2] Photocycloaddition Reactions
title_full A Chiral Thiourea as a Template for Enantioselective Intramolecular [2 + 2] Photocycloaddition Reactions
title_fullStr A Chiral Thiourea as a Template for Enantioselective Intramolecular [2 + 2] Photocycloaddition Reactions
title_full_unstemmed A Chiral Thiourea as a Template for Enantioselective Intramolecular [2 + 2] Photocycloaddition Reactions
title_short A Chiral Thiourea as a Template for Enantioselective Intramolecular [2 + 2] Photocycloaddition Reactions
title_sort chiral thiourea as a template for enantioselective intramolecular [2 + 2] photocycloaddition reactions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4994062/
https://www.ncbi.nlm.nih.gov/pubmed/27258626
http://dx.doi.org/10.1021/acs.joc.6b01039
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