Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones

A bioinspired enantioselective synthesis of crinine-type alkaloids has been developed by iridium-catalyzed asymmetric hydrogenation of racemic cycloenones. The method features a biomimetic stereodivergent resolution of the substrates bearing a remote arylated quaternary stereocenter. Using this prot...

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Autores principales: Zuo, Xiao-Dong, Guo, Shu-Min, Yang, Rui, Xie, Jian-Hua, Zhou, Qi-Lin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5628337/
https://www.ncbi.nlm.nih.gov/pubmed/28989653
http://dx.doi.org/10.1039/c7sc02112g
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author Zuo, Xiao-Dong
Guo, Shu-Min
Yang, Rui
Xie, Jian-Hua
Zhou, Qi-Lin
author_facet Zuo, Xiao-Dong
Guo, Shu-Min
Yang, Rui
Xie, Jian-Hua
Zhou, Qi-Lin
author_sort Zuo, Xiao-Dong
collection PubMed
description A bioinspired enantioselective synthesis of crinine-type alkaloids has been developed by iridium-catalyzed asymmetric hydrogenation of racemic cycloenones. The method features a biomimetic stereodivergent resolution of the substrates bearing a remote arylated quaternary stereocenter. Using this protocol, 24 crinine-type alkaloids and 8 analogues were synthesized in a concise and rapid way with high yield and high enantioselectivity.
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spelling pubmed-56283372017-10-06 Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones Zuo, Xiao-Dong Guo, Shu-Min Yang, Rui Xie, Jian-Hua Zhou, Qi-Lin Chem Sci Chemistry A bioinspired enantioselective synthesis of crinine-type alkaloids has been developed by iridium-catalyzed asymmetric hydrogenation of racemic cycloenones. The method features a biomimetic stereodivergent resolution of the substrates bearing a remote arylated quaternary stereocenter. Using this protocol, 24 crinine-type alkaloids and 8 analogues were synthesized in a concise and rapid way with high yield and high enantioselectivity. Royal Society of Chemistry 2017-09-01 2017-07-03 /pmc/articles/PMC5628337/ /pubmed/28989653 http://dx.doi.org/10.1039/c7sc02112g Text en This journal is © The Royal Society of Chemistry 2017 https://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/ (https://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
Zuo, Xiao-Dong
Guo, Shu-Min
Yang, Rui
Xie, Jian-Hua
Zhou, Qi-Lin
Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones
title Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones
title_full Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones
title_fullStr Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones
title_full_unstemmed Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones
title_short Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones
title_sort bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5628337/
https://www.ncbi.nlm.nih.gov/pubmed/28989653
http://dx.doi.org/10.1039/c7sc02112g
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