A Mild, Diastereoselective Construction of Cyclic and Spirocyclic Ketals Employing a Tandem Photoisomerization/Cyclization Tactic

[Image: see text] The cyclization of trans-δ-hydroxy enones to cyclic mixed ketals routinely requires superstoichiometric strong acid. By operating under a photoisomerization regime, the cyclization of trans-δ-hydroxy enones proceeds under catalytic Brønsted acid to provide cyclic ketals or unsatura...

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Detalles Bibliográficos
Autores principales: Li, Bo, Williams, Brett D., Smith, Amos B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4295796/
https://www.ncbi.nlm.nih.gov/pubmed/25489978
http://dx.doi.org/10.1021/ol503116q
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author Li, Bo
Williams, Brett D.
Smith, Amos B.
author_facet Li, Bo
Williams, Brett D.
Smith, Amos B.
author_sort Li, Bo
collection PubMed
description [Image: see text] The cyclization of trans-δ-hydroxy enones to cyclic mixed ketals routinely requires superstoichiometric strong acid. By operating under a photoisomerization regime, the cyclization of trans-δ-hydroxy enones proceeds under catalytic Brønsted acid to provide cyclic ketals or unsaturated spiroketals in a highly diastereoselective fashion. A one-pot, two-step protocol was thus developed to provide cyclic methoxy ketals with a free β-hydroxy group for future functionalization.
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spelling pubmed-42957962015-12-09 A Mild, Diastereoselective Construction of Cyclic and Spirocyclic Ketals Employing a Tandem Photoisomerization/Cyclization Tactic Li, Bo Williams, Brett D. Smith, Amos B. Org Lett [Image: see text] The cyclization of trans-δ-hydroxy enones to cyclic mixed ketals routinely requires superstoichiometric strong acid. By operating under a photoisomerization regime, the cyclization of trans-δ-hydroxy enones proceeds under catalytic Brønsted acid to provide cyclic ketals or unsaturated spiroketals in a highly diastereoselective fashion. A one-pot, two-step protocol was thus developed to provide cyclic methoxy ketals with a free β-hydroxy group for future functionalization. American Chemical Society 2014-12-09 2015-01-02 /pmc/articles/PMC4295796/ /pubmed/25489978 http://dx.doi.org/10.1021/ol503116q Text en Copyright © 2014 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 Li, Bo
Williams, Brett D.
Smith, Amos B.
A Mild, Diastereoselective Construction of Cyclic and Spirocyclic Ketals Employing a Tandem Photoisomerization/Cyclization Tactic
title A Mild, Diastereoselective Construction of Cyclic and Spirocyclic Ketals Employing a Tandem Photoisomerization/Cyclization Tactic
title_full A Mild, Diastereoselective Construction of Cyclic and Spirocyclic Ketals Employing a Tandem Photoisomerization/Cyclization Tactic
title_fullStr A Mild, Diastereoselective Construction of Cyclic and Spirocyclic Ketals Employing a Tandem Photoisomerization/Cyclization Tactic
title_full_unstemmed A Mild, Diastereoselective Construction of Cyclic and Spirocyclic Ketals Employing a Tandem Photoisomerization/Cyclization Tactic
title_short A Mild, Diastereoselective Construction of Cyclic and Spirocyclic Ketals Employing a Tandem Photoisomerization/Cyclization Tactic
title_sort mild, diastereoselective construction of cyclic and spirocyclic ketals employing a tandem photoisomerization/cyclization tactic
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4295796/
https://www.ncbi.nlm.nih.gov/pubmed/25489978
http://dx.doi.org/10.1021/ol503116q
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