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Catalytic Asymmetric Synthesis of Tröger’s Base Analogues with Nitrogen Stereocenter
[Image: see text] Nitrogen stereocenters are common chiral units in natural products, pharmaceuticals, and chiral catalysts. However, their research has lagged largely behind, compared with carbon stereocenters and other heteroatom stereocenters. Herein, we report an efficient method for the catalyt...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9881208/ https://www.ncbi.nlm.nih.gov/pubmed/36712492 http://dx.doi.org/10.1021/acscentsci.2c01121 |
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author | Ma, Chun Sun, Yue Yang, Junfeng Guo, Hao Zhang, Junliang |
author_facet | Ma, Chun Sun, Yue Yang, Junfeng Guo, Hao Zhang, Junliang |
author_sort | Ma, Chun |
collection | PubMed |
description | [Image: see text] Nitrogen stereocenters are common chiral units in natural products, pharmaceuticals, and chiral catalysts. However, their research has lagged largely behind, compared with carbon stereocenters and other heteroatom stereocenters. Herein, we report an efficient method for the catalytic asymmetric synthesis of Tröger’s base analogues with nitrogen stereocenters via palladium catalysis and home-developed GF-Phos. It allows rapid construction of a new rigid cleft-like structure with both a C- and a N-stereogenic center in high efficiency and selectivity. A variety of applications as a chiral organocatalyst and metallic catalyst precursors were demonstrated. Furthermore, DFT calculations suggest that the NH···O hydrogen bonding and weak interaction between the substrate and ligand are crucial for the excellent enantioselectivity control. |
format | Online Article Text |
id | pubmed-9881208 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-98812082023-01-28 Catalytic Asymmetric Synthesis of Tröger’s Base Analogues with Nitrogen Stereocenter Ma, Chun Sun, Yue Yang, Junfeng Guo, Hao Zhang, Junliang ACS Cent Sci [Image: see text] Nitrogen stereocenters are common chiral units in natural products, pharmaceuticals, and chiral catalysts. However, their research has lagged largely behind, compared with carbon stereocenters and other heteroatom stereocenters. Herein, we report an efficient method for the catalytic asymmetric synthesis of Tröger’s base analogues with nitrogen stereocenters via palladium catalysis and home-developed GF-Phos. It allows rapid construction of a new rigid cleft-like structure with both a C- and a N-stereogenic center in high efficiency and selectivity. A variety of applications as a chiral organocatalyst and metallic catalyst precursors were demonstrated. Furthermore, DFT calculations suggest that the NH···O hydrogen bonding and weak interaction between the substrate and ligand are crucial for the excellent enantioselectivity control. American Chemical Society 2023-01-04 /pmc/articles/PMC9881208/ /pubmed/36712492 http://dx.doi.org/10.1021/acscentsci.2c01121 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Ma, Chun Sun, Yue Yang, Junfeng Guo, Hao Zhang, Junliang Catalytic Asymmetric Synthesis of Tröger’s Base Analogues with Nitrogen Stereocenter |
title | Catalytic Asymmetric
Synthesis of Tröger’s
Base Analogues with Nitrogen Stereocenter |
title_full | Catalytic Asymmetric
Synthesis of Tröger’s
Base Analogues with Nitrogen Stereocenter |
title_fullStr | Catalytic Asymmetric
Synthesis of Tröger’s
Base Analogues with Nitrogen Stereocenter |
title_full_unstemmed | Catalytic Asymmetric
Synthesis of Tröger’s
Base Analogues with Nitrogen Stereocenter |
title_short | Catalytic Asymmetric
Synthesis of Tröger’s
Base Analogues with Nitrogen Stereocenter |
title_sort | catalytic asymmetric
synthesis of tröger’s
base analogues with nitrogen stereocenter |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9881208/ https://www.ncbi.nlm.nih.gov/pubmed/36712492 http://dx.doi.org/10.1021/acscentsci.2c01121 |
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