Combining Silver Catalysis and Organocatalysis: A Sequential Michael Addition/Hydroalkoxylation One-Pot Approach to Annulated Coumarins

[Image: see text] A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed. By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good t...

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Autores principales: Hack, Daniel, Chauhan, Pankaj, Deckers, Kristina, Hermann, Gary N., Mertens, Lucas, Raabe, Gerhard, Enders, Dieter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4608575/
https://www.ncbi.nlm.nih.gov/pubmed/25250728
http://dx.doi.org/10.1021/ol502551u
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author Hack, Daniel
Chauhan, Pankaj
Deckers, Kristina
Hermann, Gary N.
Mertens, Lucas
Raabe, Gerhard
Enders, Dieter
author_facet Hack, Daniel
Chauhan, Pankaj
Deckers, Kristina
Hermann, Gary N.
Mertens, Lucas
Raabe, Gerhard
Enders, Dieter
author_sort Hack, Daniel
collection PubMed
description [Image: see text] A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed. By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good to excellent enantioselectivities (up to 99% ee) via a Michael addition/hydroalkoxylation reaction. Depending on the substituents on the enynone, the synthesis of annulated six-membered rings is also feasible.
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spelling pubmed-46085752015-10-22 Combining Silver Catalysis and Organocatalysis: A Sequential Michael Addition/Hydroalkoxylation One-Pot Approach to Annulated Coumarins Hack, Daniel Chauhan, Pankaj Deckers, Kristina Hermann, Gary N. Mertens, Lucas Raabe, Gerhard Enders, Dieter Org Lett [Image: see text] A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed. By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good to excellent enantioselectivities (up to 99% ee) via a Michael addition/hydroalkoxylation reaction. Depending on the substituents on the enynone, the synthesis of annulated six-membered rings is also feasible. American Chemical Society 2014-09-24 2014-10-03 /pmc/articles/PMC4608575/ /pubmed/25250728 http://dx.doi.org/10.1021/ol502551u Text en Copyright © 2014 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Hack, Daniel
Chauhan, Pankaj
Deckers, Kristina
Hermann, Gary N.
Mertens, Lucas
Raabe, Gerhard
Enders, Dieter
Combining Silver Catalysis and Organocatalysis: A Sequential Michael Addition/Hydroalkoxylation One-Pot Approach to Annulated Coumarins
title Combining Silver Catalysis and Organocatalysis: A Sequential Michael Addition/Hydroalkoxylation One-Pot Approach to Annulated Coumarins
title_full Combining Silver Catalysis and Organocatalysis: A Sequential Michael Addition/Hydroalkoxylation One-Pot Approach to Annulated Coumarins
title_fullStr Combining Silver Catalysis and Organocatalysis: A Sequential Michael Addition/Hydroalkoxylation One-Pot Approach to Annulated Coumarins
title_full_unstemmed Combining Silver Catalysis and Organocatalysis: A Sequential Michael Addition/Hydroalkoxylation One-Pot Approach to Annulated Coumarins
title_short Combining Silver Catalysis and Organocatalysis: A Sequential Michael Addition/Hydroalkoxylation One-Pot Approach to Annulated Coumarins
title_sort combining silver catalysis and organocatalysis: a sequential michael addition/hydroalkoxylation one-pot approach to annulated coumarins
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4608575/
https://www.ncbi.nlm.nih.gov/pubmed/25250728
http://dx.doi.org/10.1021/ol502551u
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