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.

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[ 1 ] [Li, Xinglong]Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, State Key Lab Struct Chem, Fuzhou 350100, Fujian, Peoples R China
[ 2 ] [Kong, Xiangwen]Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, State Key Lab Struct Chem, Fuzhou 350100, Fujian, Peoples R China
[ 3 ] [Yang, Shuang]Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, State Key Lab Struct Chem, Fuzhou 350100, Fujian, Peoples R China
[ 4 ] [Fang, Xinqiang]Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, State Key Lab Struct Chem, Fuzhou 350100, Fujian, Peoples R China
[ 5 ] [Li, Xinglong]Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350100, Fujian, Peoples R China
[ 6 ] [Kong, Xiangwen]Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350100, Fujian, Peoples R China
[ 7 ] [Yang, Shuang]Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350100, Fujian, Peoples R China
[ 8 ] [Fang, Xinqiang]Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350100, Fujian, Peoples R China
[ 9 ] [Zhan, Xinyue]Fuzhou Univ, Coll Chem, Fuzhou 350116, Fujian, Peoples R China
[ 10 ] [Zeng, Min]Fuzhou Univ, Coll Chem, Fuzhou 350116, Fujian, Peoples R China
[ 11 ] [Meng, Miao]Jinan Univ, Dept Chem, Guangzhou 510632, Guangdong, Peoples R China

Reprint 's Address：

[Yang, Shuang]Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, State Key Lab Struct Chem, Fuzhou 350100, Fujian, Peoples R China;;[Fang, Xinqiang]Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, State Key Lab Struct Chem, Fuzhou 350100, Fujian, Peoples R China;;[Yang, Shuang]Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350100, Fujian, Peoples R China;;[Fang, Xinqiang]Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350100, Fujian, Peoples R China

Email：

yangshuang@fjirsm.ac.cn |
xqfang@fjirsm.ac.cn

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Bifunctional thiourea-catalyzed asymmetric inverse-electron-demand diels-alder reaction of allyl ketones and vinyl 1,2-diketones via dienolate intermediate
2019，Organic Letters

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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 Discipline： CHEMISTRY;

ESI HC Threshold：184

JCR Journal Grade：1

CAS Journal Grade：1

Cited Count：

WoS CC Cited Count： 43

SCOPUS Cited Count： 41

ESI Highly Cited Papers on the List： 0 Unfold All

WanFang Cited Count：

Chinese Cited Count：

30 Days PV： 2

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