Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations

2,2-Disubstituted cyclic 1,3-diketones containing a tethered electron-deficient alkene undergo chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations to give bridged bicyclic products in high enantioselectivities. Both bicyclo[3.2.1]octanes and bicyclo[3.3.1]nonanes are accessible usin...

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Autores principales: Burns, Alan R., Madec, Amaël G. E., Low, Darryl W., Roy, Iain D., Lam, Hon Wai
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5659222/
https://www.ncbi.nlm.nih.gov/pubmed/29511516
http://dx.doi.org/10.1039/c5sc00753d
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author Burns, Alan R.
Madec, Amaël G. E.
Low, Darryl W.
Roy, Iain D.
Lam, Hon Wai
author_facet Burns, Alan R.
Madec, Amaël G. E.
Low, Darryl W.
Roy, Iain D.
Lam, Hon Wai
author_sort Burns, Alan R.
collection PubMed
description 2,2-Disubstituted cyclic 1,3-diketones containing a tethered electron-deficient alkene undergo chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations to give bridged bicyclic products in high enantioselectivities. Both bicyclo[3.2.1]octanes and bicyclo[3.3.1]nonanes are accessible using this methodology.
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spelling pubmed-56592222018-03-06 Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations Burns, Alan R. Madec, Amaël G. E. Low, Darryl W. Roy, Iain D. Lam, Hon Wai Chem Sci Chemistry 2,2-Disubstituted cyclic 1,3-diketones containing a tethered electron-deficient alkene undergo chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations to give bridged bicyclic products in high enantioselectivities. Both bicyclo[3.2.1]octanes and bicyclo[3.3.1]nonanes are accessible using this methodology. Royal Society of Chemistry 2015-06-01 2015-04-30 /pmc/articles/PMC5659222/ /pubmed/29511516 http://dx.doi.org/10.1039/c5sc00753d Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Burns, Alan R.
Madec, Amaël G. E.
Low, Darryl W.
Roy, Iain D.
Lam, Hon Wai
Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations
title Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations
title_full Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations
title_fullStr Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations
title_full_unstemmed Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations
title_short Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations
title_sort enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing michael cyclizations
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5659222/
https://www.ncbi.nlm.nih.gov/pubmed/29511516
http://dx.doi.org/10.1039/c5sc00753d
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