Development of a [2 + 2]-Nitroso/Alkene Cycloaddition Using Sodium Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate Catalyst: Controlled Chemoselectivity of Two Equilibrating Isomeric Intermediates

Jia-Xuan Chen; Prakash D. Jadhav; Ching-Nung Chen; Rai-Shung Liu

doi:10.1021/acs.orglett.1c01987

Development of a [2 + 2]-Nitroso/Alkene Cycloaddition Using Sodium Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate Catalyst: Controlled Chemoselectivity of Two Equilibrating Isomeric Intermediates

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Development of a [2 + 2]-Nitroso/Alkene Cycloaddition Using Sodium Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate Catalyst: Controlled Chemoselectivity of Two Equilibrating Isomeric Intermediates

Jia-Xuan Chen, Prakash D. Jadhav, Ching-Nung Chen 和 Rai-Shung Liu

Organic Letters, 卷.23(16), 頁碼.6246-6251

08/2021

DOI: https://doi.org/10.1021/acs.orglett.1c01987

摘要

Biochemistry

Physical and Theoretical Chemistry

Organic Chemistry

Sodium tetrakis[3,5-bis(trifluoromethyl)-phenyl]borate (NaBArF) catalyzes the [2 + 2] cycloaddition of 1,4-disubstituted cyclopenta-1,3-dien-2-yl esters with nitrsobenzene in toluene, affording two isolable regioisomers of 6-oxa-7-azabicyclo[3.2.0] heptanes, which thermally rearrange into the same 4-aminocyclopent-1-en-3-ones. In the case of 4-substituted cyclopenta-1,3-dien-2-yl esters, their initial [2 + 2] cycloaddition intermediates undergo a rapid ring expansion to afford six-membered piperidone derivatives efficiently.

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題名: Development of a [2 + 2]-Nitroso/Alkene Cycloaddition Using Sodium Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate Catalyst: Controlled Chemoselectivity of Two Equilibrating Isomeric Intermediates
翻譯題名: Development of a [2 + 2]-Nitroso/Alkene Cycloaddition Using Sodium Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate Catalyst: Controlled Chemoselectivity of Two Equilibrating Isomeric Intermediates
創作者：: Jia-Xuan Chen (作者) - Frontier Research Center of Matter Science and Technology , Department of Chemistry , National Tsing-Hua University
Prakash D. Jadhav (作者) - National Tsing Hua University
Ching-Nung Chen (作者) - Frontier Research Center of Matter Science and Technology , Department of Chemistry , National Tsing-Hua University
Rai-Shung Liu (作者) - Frontier Research Center of Matter Science and Technology , Department of Chemistry , National Tsing-Hua University
學術資源類型: 期刊文章
出版日期: 08/2021
出版資訊: Organic Letters, 卷.23(16), 頁碼.6246-6251
語言: 英語

Development of a [2 + 2]-Nitroso/Alkene Cycloaddition Using Sodium Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate Catalyst: Controlled Chemoselectivity of Two Equilibrating Isomeric Intermediates

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