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Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid
Enantioselective intramolecular [3 + 2] annulation of chalcones bearing an allene moiety has been successfully developed. The reaction was effectively promoted by amino acid-derived phosphines, in combination with achiral Brønsted acids. Dihydrocoumarin architectures were constructed in high yields...
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/PMC5618691/ https://www.ncbi.nlm.nih.gov/pubmed/28970906 http://dx.doi.org/10.1039/c7sc00952f |
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author | Yao, Weijun Yu, Zhaoyuan Wen, Shan Ni, Huanzhen Ullah, Nisar Lan, Yu Lu, Yixin |
author_facet | Yao, Weijun Yu, Zhaoyuan Wen, Shan Ni, Huanzhen Ullah, Nisar Lan, Yu Lu, Yixin |
author_sort | Yao, Weijun |
collection | PubMed |
description | Enantioselective intramolecular [3 + 2] annulation of chalcones bearing an allene moiety has been successfully developed. The reaction was effectively promoted by amino acid-derived phosphines, in combination with achiral Brønsted acids. Dihydrocoumarin architectures were constructed in high yields and with excellent enantiomeric excesses. Theoretical studies via DFT calculations revealed that the hydrogen bonding network induced by achiral Brønsted acids/chiral phosphines could more efficiently distinguish between two enantioselective pathways, thus leading to enhanced enantioselectivity. |
format | Online Article Text |
id | pubmed-5618691 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-56186912017-10-02 Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid Yao, Weijun Yu, Zhaoyuan Wen, Shan Ni, Huanzhen Ullah, Nisar Lan, Yu Lu, Yixin Chem Sci Chemistry Enantioselective intramolecular [3 + 2] annulation of chalcones bearing an allene moiety has been successfully developed. The reaction was effectively promoted by amino acid-derived phosphines, in combination with achiral Brønsted acids. Dihydrocoumarin architectures were constructed in high yields and with excellent enantiomeric excesses. Theoretical studies via DFT calculations revealed that the hydrogen bonding network induced by achiral Brønsted acids/chiral phosphines could more efficiently distinguish between two enantioselective pathways, thus leading to enhanced enantioselectivity. Royal Society of Chemistry 2017-07-01 2017-05-17 /pmc/articles/PMC5618691/ /pubmed/28970906 http://dx.doi.org/10.1039/c7sc00952f 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 Yao, Weijun Yu, Zhaoyuan Wen, Shan Ni, Huanzhen Ullah, Nisar Lan, Yu Lu, Yixin Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid |
title | Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid
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title_full | Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid
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title_fullStr | Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid
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title_full_unstemmed | Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid
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title_short | Chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral Brønsted acid
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title_sort | chiral phosphine-mediated intramolecular [3 + 2] annulation: enhanced enantioselectivity by achiral brønsted acid |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5618691/ https://www.ncbi.nlm.nih.gov/pubmed/28970906 http://dx.doi.org/10.1039/c7sc00952f |
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