Gold-Catalyzed [3+2]-Annulations of α-Aryl Diazoketones with the Tetrasubstituted Alkenes of Cyclopentadienes: High Stereoselectivity and Enantioselectivity
Ching-Nung Chen
Frontier Research Center for Matter Science and Technology and Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC
Search for more papers by this authorWei-Min Cheng
Frontier Research Center for Matter Science and Technology and Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC
Search for more papers by this authorJian-Kai Wang
Frontier Research Center for Matter Science and Technology and Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC
Search for more papers by this authorTzu-Hsuan Chao
Department of Chemistry, National Cheng Kung University, East District, Tainan City, Taiwan, ROC
Search for more papers by this authorCorresponding Author
Mu-Jeng Cheng
Department of Chemistry, National Cheng Kung University, East District, Tainan City, Taiwan, ROC
Search for more papers by this authorCorresponding Author
Rai-Shung Liu
Frontier Research Center for Matter Science and Technology and Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC
Search for more papers by this authorChing-Nung Chen
Frontier Research Center for Matter Science and Technology and Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC
Search for more papers by this authorWei-Min Cheng
Frontier Research Center for Matter Science and Technology and Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC
Search for more papers by this authorJian-Kai Wang
Frontier Research Center for Matter Science and Technology and Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC
Search for more papers by this authorTzu-Hsuan Chao
Department of Chemistry, National Cheng Kung University, East District, Tainan City, Taiwan, ROC
Search for more papers by this authorCorresponding Author
Mu-Jeng Cheng
Department of Chemistry, National Cheng Kung University, East District, Tainan City, Taiwan, ROC
Search for more papers by this authorCorresponding Author
Rai-Shung Liu
Frontier Research Center for Matter Science and Technology and Department of Chemistry, National Tsing-Hua University, Hsinchu, Taiwan, ROC
Search for more papers by this authorAbstract
This work reports gold-catalyzed [3+2]-annulations of α-diazo ketones with highly substituted cyclopentadienes, affording bicyclic 2,3-dihydrofurans with high regio- and stereoselectivity. The reactions highlights the first success of tetrasubstituted alkenes to undergo [3+2]-annulations with α-diazo carbonyls. The enantioselective annulations are also achieved with high enantioselectivity using chiral forms of gold and phosphoric acid. Our mechanistic analysis supports that cyclopentadienes serve as nucleophiles to attack gold carbenes at the more substituted alkenes, yielding gold enolates that complex with chiral phosphoric acid to enhance the enantioselectivity.
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- 14Additional data to manifest the effects of solvents, phosphoric acids, and silver salts on asymmetric [3+2]-annulations are provided in the Supporting Information, Tables S2, S3 and Eqs. (s1),(s2).
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