Palladium-Catalyzed Asymmetric [3+2] Cycloaddition of Vinylethylene Carbonates with 2-Arylidene-1,3-Indandiones: Synthesis of Tetrahydrofuran-Fused Spirocyclic 1,3-Indandiones

被引：10

作者：

Zhang, Huihui ^{[1
]}

Gao, Xing ^{[2
]}

Jiang, Feng ^{[2
]}

Shi, Wangyu ^{[2
]}

Wang, Wei ^{[3
]}

Wu, Yongjun ^{[3
]}

Zhang, Cheng ^{[2
]}

Shi, Xueyan ^{[1
]}

Guo, Hongchao ^{[2
]}

机构：

[1] China Agr Univ, Coll Plant Protect, Beijing 100193, Peoples R China

[2] China Agr Univ, Dept Chem, Beijing 100193, Peoples R China

[3] Zhengzhou Univ, Coll Publ Hlth, Zhengzhou 450001, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 30期

关键词：

Asymmetric catalysis; Cycloaddition; Homogeneous catalysis; Spirocyclic compounds; DECARBOXYLATIVE CYCLOADDITION; ENANTIOSELECTIVE CONSTRUCTION; HETEROCYCLES; ALLENOATES; MICHAEL; ACCESS; WATER;

D O I：

10.1002/ejoc.202000762

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric [3+2] cycloaddition of 2-arylidene-1,3-indandiones with vinylethylene carbonates (VECs) had been achieved in the presence of Pd(2)dba(3)center dot CHCl(3)and axially chiral phosphoramidite ligand. The reaction of various substituted VECs and 2-arylidene-1,3-indandiones proceeded smoothly under mild conditions, giving the highly functionalized spirocyclic 1,3-indanedione derivatives in good to excellent yield with moderate diastereoselectivity and high enantioselectivity. The reaction on the gram scale had also been demonstrated.

引用

页码：4801 / 4804

页数：4

共 38 条

[1] [Anonymous], 2018, ANGEW CHEM, V130, P13928
[2] [Anonymous], 2017, ANGEW CHEM, V129, P2973
[3] Spirocyclic Motifs in Natural Products
Chupakhin, Evgeny
Babich, Olga
Prosekov, Alexander
Asyakina, Lyudmila
Krasavin, Mikhail
[J]. MOLECULES, 2019, 24 (22):
[4] Access to benzo-fused nine-membered heterocyclic alkenes with a trifluoromethyl carbinol moiety via a double decarboxylative formal ring-expansion process under palladium catalysis
Das, Pulakesh
Gondo, Satoshi
Nagender, Punna
Uno, Hiroto
Tokunaga, Etsuko
Shibata, Norio
[J]. CHEMICAL SCIENCE, 2018, 9 (13) : 3276 - 3281
[5] Diversity-Orientated Stereoselective Synthesis through Pd-Catalyzed Switchable Decarboxylative C-N/C-S Bond Formation in Allylic Surrogates
Deng, Lei
Kleij, Arjan W.
Yang, Weibo
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (72) : 19156 - 19161
[6] New development in the enantioselective synthesis of spiro compounds
Ding, Aishun
Meazza, Marta
Guo, Hao
Yang, Jung Woon
Rios, Ramon
[J]. CHEMICAL SOCIETY REVIEWS, 2018, 47 (15) : 5946 - 5996
[7] Catalytic nonreductive valorization of carbon dioxide into fine chemicals
Enrique Gomez, Jose
Kleij, Arjan W.
[J]. ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 71, 2019, 71 : 175 - 226
[8] Enantioselective Synthesis of Chiral Medium-Sized Cyclic Compounds via Tandem Cycloaddition/Cope Rearrangement Strategy
Gao, Xing
Xia, Miaoren
Yuan, Chunhao
Zhou, Leijie
Sun, Wei
Li, Cheng
Wu, Bo
Zhu, Dongyu
Zhang, Cheng
Zheng, Bing
Wang, Dongqi
Guo, Hongchao
[J]. ACS CATALYSIS, 2019, 9 (03): : 1645 - 1654
[9] Guo W., 2016, ANGEW CHEMIE, V128, P11203
[10] Catalytic Transformations of Functionalized Cyclic Organic Carbonates
Guo, Wusheng
Enrique Gomez, Jose
Cristofol, Alex
Xie, Jianing
Kleij, Arjan W.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (42) : 13735 - 13747

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