Highly Efficient Cascade Reaction for Selective Formation of Spirocyclobutenes from Dienallenes via Palladium-Catalyzed Oxidative Double Carbocyclization–Carbonylation–Alkynylation

[Image: see text] A highly selective cascade reaction that allows the direct transformation of dienallenes to spirocyclobutenes (spiro[3.4]octenes) as single diastereoisomers has been developed. The reaction involves formation of overall four C–C bonds and proceeds via a palladium-catalyzed oxidativ...

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Autores principales: Qiu, Youai, Yang, Bin, Zhu, Can, Bäckvall, Jan-E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5084063/
https://www.ncbi.nlm.nih.gov/pubmed/27704805
http://dx.doi.org/10.1021/jacs.6b09240
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author Qiu, Youai
Yang, Bin
Zhu, Can
Bäckvall, Jan-E.
author_facet Qiu, Youai
Yang, Bin
Zhu, Can
Bäckvall, Jan-E.
author_sort Qiu, Youai
collection PubMed
description [Image: see text] A highly selective cascade reaction that allows the direct transformation of dienallenes to spirocyclobutenes (spiro[3.4]octenes) as single diastereoisomers has been developed. The reaction involves formation of overall four C–C bonds and proceeds via a palladium-catalyzed oxidative transformation with insertion of olefin, olefin, and carbon monoxide. Under slightly different reaction conditions, an additional CO insertion takes place to give spiro[4.4]nonenes with formation of overall five C–C bonds.
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spelling pubmed-50840632016-10-31 Highly Efficient Cascade Reaction for Selective Formation of Spirocyclobutenes from Dienallenes via Palladium-Catalyzed Oxidative Double Carbocyclization–Carbonylation–Alkynylation Qiu, Youai Yang, Bin Zhu, Can Bäckvall, Jan-E. J Am Chem Soc [Image: see text] A highly selective cascade reaction that allows the direct transformation of dienallenes to spirocyclobutenes (spiro[3.4]octenes) as single diastereoisomers has been developed. The reaction involves formation of overall four C–C bonds and proceeds via a palladium-catalyzed oxidative transformation with insertion of olefin, olefin, and carbon monoxide. Under slightly different reaction conditions, an additional CO insertion takes place to give spiro[4.4]nonenes with formation of overall five C–C bonds. American Chemical Society 2016-10-05 2016-10-26 /pmc/articles/PMC5084063/ /pubmed/27704805 http://dx.doi.org/10.1021/jacs.6b09240 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 Qiu, Youai
Yang, Bin
Zhu, Can
Bäckvall, Jan-E.
Highly Efficient Cascade Reaction for Selective Formation of Spirocyclobutenes from Dienallenes via Palladium-Catalyzed Oxidative Double Carbocyclization–Carbonylation–Alkynylation
title Highly Efficient Cascade Reaction for Selective Formation of Spirocyclobutenes from Dienallenes via Palladium-Catalyzed Oxidative Double Carbocyclization–Carbonylation–Alkynylation
title_full Highly Efficient Cascade Reaction for Selective Formation of Spirocyclobutenes from Dienallenes via Palladium-Catalyzed Oxidative Double Carbocyclization–Carbonylation–Alkynylation
title_fullStr Highly Efficient Cascade Reaction for Selective Formation of Spirocyclobutenes from Dienallenes via Palladium-Catalyzed Oxidative Double Carbocyclization–Carbonylation–Alkynylation
title_full_unstemmed Highly Efficient Cascade Reaction for Selective Formation of Spirocyclobutenes from Dienallenes via Palladium-Catalyzed Oxidative Double Carbocyclization–Carbonylation–Alkynylation
title_short Highly Efficient Cascade Reaction for Selective Formation of Spirocyclobutenes from Dienallenes via Palladium-Catalyzed Oxidative Double Carbocyclization–Carbonylation–Alkynylation
title_sort highly efficient cascade reaction for selective formation of spirocyclobutenes from dienallenes via palladium-catalyzed oxidative double carbocyclization–carbonylation–alkynylation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5084063/
https://www.ncbi.nlm.nih.gov/pubmed/27704805
http://dx.doi.org/10.1021/jacs.6b09240
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