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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Royal Society of Chemistry
2017
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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. |
format | Online Article Text |
id | pubmed-5358503 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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
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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
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title_short | 6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis
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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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