Bifunctional thiourea-catalyzed asymmetric inverse-electron-demand diels-alder reaction of allyl ketones and vinyl 1,2-diketones via dienolate intermediate - Details

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Abstract：

Inverse-electron-demand　Diels-Alder　reactions　have　attracted　intense　research　focus.　However,　enolate　and　enamine　are　the　most　employed　intermediates　to　realize　such　transformation,　and　the　use　of　dienolate　intermediate　remains　elusive.　Reported　herein　is　the　asymmetric　inverse-electron-demand　oxa-Diels-Alder　reaction　between　allyl　ketones　and　alkenyl　1,2-diketones　using　a　bifunctional　thiourea　catalyst.　The　reaction　afforded　various　highly　functionalized　dihydropyrans　with　good　to　excellent　enantioselectivities　under　mild　conditions,　and　further　novel　transformations　on　the　products　have　also　been　realized.　©　2019　American　Chemical　Society.

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[ 1 ] [Li, X.]State Key Laboratory of Structural Chemistry, Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou, 350100, China
[ 2 ] [Kong, X.]State Key Laboratory of Structural Chemistry, Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou, 350100, China
[ 3 ] [Yang, S.]State Key Laboratory of Structural Chemistry, Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou, 350100, China
[ 4 ] [Meng, M.]Department of Chemistry, Jinan University, Guangzhou, 510632, China
[ 5 ] [Zhan, X.]College of Chemistry, Fuzhou University, Fuzhou, 350116, China
[ 6 ] [Zeng, M.]College of Chemistry, Fuzhou University, Fuzhou, 350116, China
[ 7 ] [Fang, X.]State Key Laboratory of Structural Chemistry, Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou, 350100, China

Reprint 's Address：

[Yang, S.]State Key Laboratory of Structural Chemistry, Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of SciencesChina

Email：

yangshuang@fjirsm.ac.cn

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Organic Letters

ISSN： 1523-7060

Year： 2019

Issue： 7

Volume： 21

Page： 1979-1983

6 . 0 9 1

JCR@2019

4 . 9 0 0

JCR@2023

ESI HC Threshold：184

JCR Journal Grade：1

CAS Journal Grade：1

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WoS CC Cited Count：

SCOPUS Cited Count： 45

ESI Highly Cited Papers on the List： 0 Unfold All

WanFang Cited Count：

Chinese Cited Count：

30 Days PV： 1

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