Direct access to spirocycles by Pd/WingPhos-catalyzed enantioselective cycloaddition of 1,3-enynes
Spirocycles play an important role in drug discovery and development. The direct, catalytic, and enantioselective synthesis of spirocycles from readily available starting materials and in an atom economic manner remains a highly sought-after task in organic synthesis. Herein, an enantioselective Pd-...
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| Published in | Nature communications Vol. 12; no. 1; pp. 5667 - 11 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
London
Nature Publishing Group UK
27.09.2021
Nature Publishing Group Nature Portfolio |
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| Abstract | Spirocycles play an important role in drug discovery and development. The direct, catalytic, and enantioselective synthesis of spirocycles from readily available starting materials and in an atom economic manner remains a highly sought-after task in organic synthesis. Herein, an enantioselective Pd-hydride-catalyzed cycloaddition method for the synthesis of spirocyclic compounds directly from two classes of commonly available starting materials, 1,3-enynes and cyclic carbon−hydrogen (C−H) bonds, is reported. The reactions employ a chiral Pd/WingPhos catalyst to both suppress the formation of bis-allenyl by-products and control the stereoselectivity. 1,3-Enynes are used as dielectrophilic four-carbon units in the cycloaddition reactions, which also enables an enyne substrate-directed enantioselectivity switch with good levels of stereocontrol. The present spirocycle synthesis tolerates a broad range of functional groups of 1,3-enyne substrates, including alcohols, esters, nitriles, halides, and olefins. A variety of diverse cyclic nucleophiles, including pharmaceutically important heterocycles and carbocycles, can be flexibly incorporated with spiro scaffolds.
Spirocycles are traditionally difficult structures to synthesize due to the congested nature of the central atom. Here the authors show a method to synthesize quaternary carbon spirocycles in one step from 1,3-enynes and pyrazolidine-type heterocycles, both relatively unactivated structures, proceeding via palladium catalysis. |
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| AbstractList | Spirocycles play an important role in drug discovery and development. The direct, catalytic, and enantioselective synthesis of spirocycles from readily available starting materials and in an atom economic manner remains a highly sought-after task in organic synthesis. Herein, an enantioselective Pd-hydride-catalyzed cycloaddition method for the synthesis of spirocyclic compounds directly from two classes of commonly available starting materials, 1,3-enynes and cyclic carbon−hydrogen (C−H) bonds, is reported. The reactions employ a chiral Pd/WingPhos catalyst to both suppress the formation of bis-allenyl by-products and control the stereoselectivity. 1,3-Enynes are used as dielectrophilic four-carbon units in the cycloaddition reactions, which also enables an enyne substrate-directed enantioselectivity switch with good levels of stereocontrol. The present spirocycle synthesis tolerates a broad range of functional groups of 1,3-enyne substrates, including alcohols, esters, nitriles, halides, and olefins. A variety of diverse cyclic nucleophiles, including pharmaceutically important heterocycles and carbocycles, can be flexibly incorporated with spiro scaffolds.
Spirocycles are traditionally difficult structures to synthesize due to the congested nature of the central atom. Here the authors show a method to synthesize quaternary carbon spirocycles in one step from 1,3-enynes and pyrazolidine-type heterocycles, both relatively unactivated structures, proceeding via palladium catalysis. Spirocycles play an important role in drug discovery and development. The direct, catalytic, and enantioselective synthesis of spirocycles from readily available starting materials and in an atom economic manner remains a highly sought-after task in organic synthesis. Herein, an enantioselective Pd-hydride-catalyzed cycloaddition method for the synthesis of spirocyclic compounds directly from two classes of commonly available starting materials, 1,3-enynes and cyclic carbon-hydrogen (C-H) bonds, is reported. The reactions employ a chiral Pd/WingPhos catalyst to both suppress the formation of bis-allenyl by-products and control the stereoselectivity. 1,3-Enynes are used as dielectrophilic four-carbon units in the cycloaddition reactions, which also enables an enyne substrate-directed enantioselectivity switch with good levels of stereocontrol. The present spirocycle synthesis tolerates a broad range of functional groups of 1,3-enyne substrates, including alcohols, esters, nitriles, halides, and olefins. A variety of diverse cyclic nucleophiles, including pharmaceutically important heterocycles and carbocycles, can be flexibly incorporated with spiro scaffolds.Spirocycles play an important role in drug discovery and development. The direct, catalytic, and enantioselective synthesis of spirocycles from readily available starting materials and in an atom economic manner remains a highly sought-after task in organic synthesis. Herein, an enantioselective Pd-hydride-catalyzed cycloaddition method for the synthesis of spirocyclic compounds directly from two classes of commonly available starting materials, 1,3-enynes and cyclic carbon-hydrogen (C-H) bonds, is reported. The reactions employ a chiral Pd/WingPhos catalyst to both suppress the formation of bis-allenyl by-products and control the stereoselectivity. 1,3-Enynes are used as dielectrophilic four-carbon units in the cycloaddition reactions, which also enables an enyne substrate-directed enantioselectivity switch with good levels of stereocontrol. The present spirocycle synthesis tolerates a broad range of functional groups of 1,3-enyne substrates, including alcohols, esters, nitriles, halides, and olefins. A variety of diverse cyclic nucleophiles, including pharmaceutically important heterocycles and carbocycles, can be flexibly incorporated with spiro scaffolds. Spirocycles play an important role in drug discovery and development. The direct, catalytic, and enantioselective synthesis of spirocycles from readily available starting materials and in an atom economic manner remains a highly sought-after task in organic synthesis. Herein, an enantioselective Pd-hydride-catalyzed cycloaddition method for the synthesis of spirocyclic compounds directly from two classes of commonly available starting materials, 1,3-enynes and cyclic carbon−hydrogen (C−H) bonds, is reported. The reactions employ a chiral Pd/WingPhos catalyst to both suppress the formation of bis-allenyl by-products and control the stereoselectivity. 1,3-Enynes are used as dielectrophilic four-carbon units in the cycloaddition reactions, which also enables an enyne substrate-directed enantioselectivity switch with good levels of stereocontrol. The present spirocycle synthesis tolerates a broad range of functional groups of 1,3-enyne substrates, including alcohols, esters, nitriles, halides, and olefins. A variety of diverse cyclic nucleophiles, including pharmaceutically important heterocycles and carbocycles, can be flexibly incorporated with spiro scaffolds. Spirocycles play an important role in drug discovery and development. The direct, catalytic, and enantioselective synthesis of spirocycles from readily available starting materials and in an atom economic manner remains a highly sought-after task in organic synthesis. Herein, an enantioselective Pd-hydride-catalyzed cycloaddition method for the synthesis of spirocyclic compounds directly from two classes of commonly available starting materials, 1,3-enynes and cyclic carbon−hydrogen (C−H) bonds, is reported. The reactions employ a chiral Pd/WingPhos catalyst to both suppress the formation of bis-allenyl by-products and control the stereoselectivity. 1,3-Enynes are used as dielectrophilic four-carbon units in the cycloaddition reactions, which also enables an enyne substrate-directed enantioselectivity switch with good levels of stereocontrol. The present spirocycle synthesis tolerates a broad range of functional groups of 1,3-enyne substrates, including alcohols, esters, nitriles, halides, and olefins. A variety of diverse cyclic nucleophiles, including pharmaceutically important heterocycles and carbocycles, can be flexibly incorporated with spiro scaffolds.Spirocycles are traditionally difficult structures to synthesize due to the congested nature of the central atom. Here the authors show a method to synthesize quaternary carbon spirocycles in one step from 1,3-enynes and pyrazolidine-type heterocycles, both relatively unactivated structures, proceeding via palladium catalysis. Spirocycles are traditionally difficult structures to synthesize due to the congested nature of the central atom. Here the authors show a method to synthesize quaternary carbon spirocycles in one step from 1,3-enynes and pyrazolidine-type heterocycles, both relatively unactivated structures, proceeding via palladium catalysis. |
| ArticleNumber | 5667 |
| Author | Shao, Zhihui Li, Xiaoguang Wang, Zheng Wang, Ran Li, Long Deng, Yuhua Peng, Fangzhi Wang, Shan Luo, Pengfei |
| Author_xml | – sequence: 1 givenname: Long surname: Li fullname: Li, Long organization: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan Provincial Center for Research & Development of Natural Products, and State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan University – sequence: 2 givenname: Shan surname: Wang fullname: Wang, Shan organization: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan Provincial Center for Research & Development of Natural Products, and State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan University – sequence: 3 givenname: Pengfei surname: Luo fullname: Luo, Pengfei organization: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan Provincial Center for Research & Development of Natural Products, and State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan University – sequence: 4 givenname: Ran surname: Wang fullname: Wang, Ran organization: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan Provincial Center for Research & Development of Natural Products, and State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan University – sequence: 5 givenname: Zheng orcidid: 0000-0002-7560-2618 surname: Wang fullname: Wang, Zheng organization: Kunming Institute of Physics – sequence: 6 givenname: Xiaoguang orcidid: 0000-0001-9979-053X surname: Li fullname: Li, Xiaoguang organization: Institute for Advanced Study, Shenzhen University – sequence: 7 givenname: Yuhua surname: Deng fullname: Deng, Yuhua organization: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan Provincial Center for Research & Development of Natural Products, and State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan University – sequence: 8 givenname: Fangzhi surname: Peng fullname: Peng, Fangzhi organization: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan Provincial Center for Research & Development of Natural Products, and State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan University – sequence: 9 givenname: Zhihui orcidid: 0000-0003-4531-3417 surname: Shao fullname: Shao, Zhihui email: zhihui_shao@hotmail.com organization: Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan Provincial Center for Research & Development of Natural Products, and State Key Laboratory for Conservation and Utilization of Bio-Resources in Yunnan, Yunnan University |
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| Copyright | The Author(s) 2021 The Author(s) 2021. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. 2021. The Author(s). |
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| DOI | 10.1038/s41467-021-25981-x |
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| Snippet | Spirocycles play an important role in drug discovery and development. The direct, catalytic, and enantioselective synthesis of spirocycles from readily... Spirocycles are traditionally difficult structures to synthesize due to the congested nature of the central atom. Here the authors show a method to synthesize... |
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| Title | Direct access to spirocycles by Pd/WingPhos-catalyzed enantioselective cycloaddition of 1,3-enynes |
| URI | https://link.springer.com/article/10.1038/s41467-021-25981-x https://www.proquest.com/docview/2576737589 https://www.proquest.com/docview/2577457779 https://pubmed.ncbi.nlm.nih.gov/PMC8476582 https://doaj.org/article/4d3eba8180b049f1b3931c209daf7c4b |
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