6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis

The catalytic enantioselective 6-exo-trig Michael addition-lactonization of enone-acid substrates to form cis-chromenones with high diastereo- and enantiocontrol was developed using the commercially available isothiourea tetramisole. An acidic workup proved necessary to minimize product epimerizatio...

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Autores principales: Neyyappadath, Rifahath M., Cordes, David B., Slawin, Alexandra M. Z., Smith, Andrew D.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5358503/
https://www.ncbi.nlm.nih.gov/pubmed/28133660
http://dx.doi.org/10.1039/c6cc10178j
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author Neyyappadath, Rifahath M.
Cordes, David B.
Slawin, Alexandra M. Z.
Smith, Andrew D.
author_facet Neyyappadath, Rifahath M.
Cordes, David B.
Slawin, Alexandra M. Z.
Smith, Andrew D.
author_sort Neyyappadath, Rifahath M.
collection PubMed
description The catalytic enantioselective 6-exo-trig Michael addition-lactonization of enone-acid substrates to form cis-chromenones with high diastereo- and enantiocontrol was developed using the commercially available isothiourea tetramisole. An acidic workup proved necessary to minimize product epimerization and maximize product er, providing cis-chromenones in excellent yield, and with excellent diastereo- and enantioselectivity.
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spelling pubmed-53585032017-05-15 6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis Neyyappadath, Rifahath M. Cordes, David B. Slawin, Alexandra M. Z. Smith, Andrew D. Chem Commun (Camb) Chemistry The catalytic enantioselective 6-exo-trig Michael addition-lactonization of enone-acid substrates to form cis-chromenones with high diastereo- and enantiocontrol was developed using the commercially available isothiourea tetramisole. An acidic workup proved necessary to minimize product epimerization and maximize product er, providing cis-chromenones in excellent yield, and with excellent diastereo- and enantioselectivity. Royal Society of Chemistry 2017-02-28 2017-01-19 /pmc/articles/PMC5358503/ /pubmed/28133660 http://dx.doi.org/10.1039/c6cc10178j Text en This journal is © The Royal Society of Chemistry 2017 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Neyyappadath, Rifahath M.
Cordes, David B.
Slawin, Alexandra M. Z.
Smith, Andrew D.
6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis
title 6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis
title_full 6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis
title_fullStr 6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis
title_full_unstemmed 6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis
title_short 6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis
title_sort 6-exo-trig michael addition-lactonizations for catalytic enantioselective chromenone synthesis
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5358503/
https://www.ncbi.nlm.nih.gov/pubmed/28133660
http://dx.doi.org/10.1039/c6cc10178j
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