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Efficient Synthesis of Chiral Trisubstituted 1,2‐Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes
An N,N′‐dioxide/scandium(III) complex catalyzed, highly efficient conjugate addition of malonic esters to enynes is described. A range of trisubstituted 1,2‐allenyl ketones were obtained in high yields (up to 99 %) with good d.r. (up to 95/5) and excellent ee values (97 %–99 %). Moreover, the produc...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2015
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4738401/ https://www.ncbi.nlm.nih.gov/pubmed/26694204 http://dx.doi.org/10.1002/anie.201509455 |
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author | Yao, Qian Liao, Yuting Lin, Lili Lin, Xiaobin Ji, Jie Liu, Xiaohua Feng, Xiaoming |
author_facet | Yao, Qian Liao, Yuting Lin, Lili Lin, Xiaobin Ji, Jie Liu, Xiaohua Feng, Xiaoming |
author_sort | Yao, Qian |
collection | PubMed |
description | An N,N′‐dioxide/scandium(III) complex catalyzed, highly efficient conjugate addition of malonic esters to enynes is described. A range of trisubstituted 1,2‐allenyl ketones were obtained in high yields (up to 99 %) with good d.r. (up to 95/5) and excellent ee values (97 %–99 %). Moreover, the products could be easily transformed into chiral furan and 5‐hydroxypyrazoline derivatives, both of which are important skeletons of many biologically active compounds and pharmacologicals. |
format | Online Article Text |
id | pubmed-4738401 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-47384012016-02-12 Efficient Synthesis of Chiral Trisubstituted 1,2‐Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes Yao, Qian Liao, Yuting Lin, Lili Lin, Xiaobin Ji, Jie Liu, Xiaohua Feng, Xiaoming Angew Chem Int Ed Engl Communications An N,N′‐dioxide/scandium(III) complex catalyzed, highly efficient conjugate addition of malonic esters to enynes is described. A range of trisubstituted 1,2‐allenyl ketones were obtained in high yields (up to 99 %) with good d.r. (up to 95/5) and excellent ee values (97 %–99 %). Moreover, the products could be easily transformed into chiral furan and 5‐hydroxypyrazoline derivatives, both of which are important skeletons of many biologically active compounds and pharmacologicals. John Wiley and Sons Inc. 2015-12-22 2016-01 /pmc/articles/PMC4738401/ /pubmed/26694204 http://dx.doi.org/10.1002/anie.201509455 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Communications Yao, Qian Liao, Yuting Lin, Lili Lin, Xiaobin Ji, Jie Liu, Xiaohua Feng, Xiaoming Efficient Synthesis of Chiral Trisubstituted 1,2‐Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes |
title | Efficient Synthesis of Chiral Trisubstituted 1,2‐Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes |
title_full | Efficient Synthesis of Chiral Trisubstituted 1,2‐Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes |
title_fullStr | Efficient Synthesis of Chiral Trisubstituted 1,2‐Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes |
title_full_unstemmed | Efficient Synthesis of Chiral Trisubstituted 1,2‐Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes |
title_short | Efficient Synthesis of Chiral Trisubstituted 1,2‐Allenyl Ketones by Catalytic Asymmetric Conjugate Addition of Malonic Esters to Enynes |
title_sort | efficient synthesis of chiral trisubstituted 1,2‐allenyl ketones by catalytic asymmetric conjugate addition of malonic esters to enynes |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4738401/ https://www.ncbi.nlm.nih.gov/pubmed/26694204 http://dx.doi.org/10.1002/anie.201509455 |
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