Reactivity of ynamides in catalytic intermolecular annulations
Ynamides are unique alkynes with a carbon-carbon triple bond directly attached to the nitrogen atom bearing an electron-withdrawing group. The alkyne is strongly polarized by the electron-donating nitrogen atom, but its high reactivity can be finely tempered by the electron-withdrawing group. Accord...
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| Published in | Chemical Society reviews Vol. 5; no. 4; pp. 2582 - 2625 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Royal Society of Chemistry
01.03.2021
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| Subjects | |
| Online Access | Get full text |
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| Summary: | Ynamides are unique alkynes with a carbon-carbon triple bond directly attached to the nitrogen atom bearing an electron-withdrawing group. The alkyne is strongly polarized by the electron-donating nitrogen atom, but its high reactivity can be finely tempered by the electron-withdrawing group. Accordingly, ynamides are endowed with both nucleophilic and electrophilic properties and their chemistry has been an active research field. The catalytic intermolecular annulations of ynamides, featuring divergent assembly of structurally important amino-heterocycles in a regioselective manner, have gained much attention over the past decade. This review aims to provide a comprehensive summary of the advances achieved in this area involving transition metal and acid catalysis. Moreover, the intermolecular annulations of ynamide analogs including ynol ethers and thioalkynes are also discussed, which can provide insights into the reactivity difference caused by the heteroatoms.
This review comprehensively summarizes the advances achieved in catalytic intermolecular annulations of ynamides from 2010 to 2020. |
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| Bibliography: | Qing-An Chen was born in 1984 in Fujian Province, China, received a BS degree from University of Science and Technology of China in 2007 and earned his PhD degree from Dalian Institute of Chemical Physics (DICP) in 2012. He worked with Prof. Vy M. Dong at the University of California Irvine as a postdoctoral fellow from 2012 to 2015. Then he joined Prof. Martin Oestreich's group at Technische Universitat Berlin as an Alexander von Humboldt Fellow. In 2017, he began his independent career at DICP, where currently he is a professor. His research interests include asymmetric synthesis and organometallic chemistry. Boshun Wan is a full professor at Dalian Institute of Chemical Physics (DICP). His research interests include asymmetric catalysis, catalytic heterocycle synthesis, and energetic material synthesis. He received his BS degree from Nanjing Normal University in 1985 and PhD degree from DICP in 1998. Then he joined DICP as a group leader. He has been a visiting professor at Northwestern University. Yan-Cheng Hu was born in Jiangsu Province, China, in 1989. He obtained his BS degree from Nanjing Normal University in 2010 and PhD degree from Dalian Institute of Chemical Physics (DICP) in 2015, under the supervision of Prof. Boshun Wan. He did his postdoctoral research with Prof. Tao Zhang at the same institute from 2015 to 2018. Later, he worked in the group of Prof. Qing-An Chen, where he is currently an associate professor. His research focuses on transition-metal catalyzed transformations of alkynes and alkenes, as well as their applications in the total synthesis of natural products. Yingying Zhao was born in Hebei Province, China, in 1990. She received her BS degree from Jiangsu University in 2013 and PhD degree from Dalian Institute of Chemical Physics (DICP) in 2018, under the guidance of Prof. Boshun Wan. Then she began her career at Liaoning Normal University, where she works on acid-catalyzed annulations of ynamides and their applications in the synthesis of biologically relevant molecules. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 ObjectType-Review-3 content type line 23 |
| ISSN: | 0306-0012 1460-4744 1460-4744 |
| DOI: | 10.1039/d0cs00283f |