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...

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Detalles Bibliográficos
Autores principales: Yao, Qian, Liao, Yuting, Lin, Lili, Lin, Xiaobin, Ji, Jie, Liu, Xiaohua, Feng, Xiaoming
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2015
Materias:
Communications
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.
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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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