NHC-Ni catalyzed enantioselective synthesis of 1,4-dienes by cross-hydroalkenylation of cyclic 1,3-dienes and heterosubstituted terminal olefins

Enantioenriched 1,4-dienes are versatile building blocks in asymmetric synthesis, therefore their efficient synthesis directly from chemical feedstock is highly sought after. Here, we show an enantioselective cross-hydroalkenylation of cyclic 1,3-diene and hetero-substituted terminal olefin by using...

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Autores principales: Chen, Yang, Dang, Liang, Ho, Chun-Yu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7210895/
https://www.ncbi.nlm.nih.gov/pubmed/32385240
http://dx.doi.org/10.1038/s41467-020-16139-2
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author Chen, Yang
Dang, Liang
Ho, Chun-Yu
author_facet Chen, Yang
Dang, Liang
Ho, Chun-Yu
author_sort Chen, Yang
collection PubMed
description Enantioenriched 1,4-dienes are versatile building blocks in asymmetric synthesis, therefore their efficient synthesis directly from chemical feedstock is highly sought after. Here, we show an enantioselective cross-hydroalkenylation of cyclic 1,3-diene and hetero-substituted terminal olefin by using a chiral [NHC-Ni(allyl)]BAr(F) catalyst. Using a structurally flexible chiral C(2) NHC-Ni design is key to access a broad scope of chiral 1,4-diene 3 or 3′ with high enantioselectivity. This study also offers insights on how to regulate chiral C(2) NHC-Ni(II) 1,3-allylic shift on cyclic diene 1 and to build sterically more hindered endocyclic chiral allylic structures on demand.
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spelling pubmed-72108952020-05-13 NHC-Ni catalyzed enantioselective synthesis of 1,4-dienes by cross-hydroalkenylation of cyclic 1,3-dienes and heterosubstituted terminal olefins Chen, Yang Dang, Liang Ho, Chun-Yu Nat Commun Article Enantioenriched 1,4-dienes are versatile building blocks in asymmetric synthesis, therefore their efficient synthesis directly from chemical feedstock is highly sought after. Here, we show an enantioselective cross-hydroalkenylation of cyclic 1,3-diene and hetero-substituted terminal olefin by using a chiral [NHC-Ni(allyl)]BAr(F) catalyst. Using a structurally flexible chiral C(2) NHC-Ni design is key to access a broad scope of chiral 1,4-diene 3 or 3′ with high enantioselectivity. This study also offers insights on how to regulate chiral C(2) NHC-Ni(II) 1,3-allylic shift on cyclic diene 1 and to build sterically more hindered endocyclic chiral allylic structures on demand. Nature Publishing Group UK 2020-05-08 /pmc/articles/PMC7210895/ /pubmed/32385240 http://dx.doi.org/10.1038/s41467-020-16139-2 Text en © The Author(s) 2020 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Chen, Yang
Dang, Liang
Ho, Chun-Yu
NHC-Ni catalyzed enantioselective synthesis of 1,4-dienes by cross-hydroalkenylation of cyclic 1,3-dienes and heterosubstituted terminal olefins
title NHC-Ni catalyzed enantioselective synthesis of 1,4-dienes by cross-hydroalkenylation of cyclic 1,3-dienes and heterosubstituted terminal olefins
title_full NHC-Ni catalyzed enantioselective synthesis of 1,4-dienes by cross-hydroalkenylation of cyclic 1,3-dienes and heterosubstituted terminal olefins
title_fullStr NHC-Ni catalyzed enantioselective synthesis of 1,4-dienes by cross-hydroalkenylation of cyclic 1,3-dienes and heterosubstituted terminal olefins
title_full_unstemmed NHC-Ni catalyzed enantioselective synthesis of 1,4-dienes by cross-hydroalkenylation of cyclic 1,3-dienes and heterosubstituted terminal olefins
title_short NHC-Ni catalyzed enantioselective synthesis of 1,4-dienes by cross-hydroalkenylation of cyclic 1,3-dienes and heterosubstituted terminal olefins
title_sort nhc-ni catalyzed enantioselective synthesis of 1,4-dienes by cross-hydroalkenylation of cyclic 1,3-dienes and heterosubstituted terminal olefins
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7210895/
https://www.ncbi.nlm.nih.gov/pubmed/32385240
http://dx.doi.org/10.1038/s41467-020-16139-2
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