Enantioselective [3+2] Formal Cycloaddition of 1-Styrylnaphthols with Quinones Catalyzed by a Chiral Phosphoric Acid

被引：40

作者：

Feng, Wang ^{[1
]}

Yang, Hui ^{[1
]}

Wang, Zhe ^{[1
]}

Gou, Bo-Bo ^{[1
]}

Chen, Jie ^{[1
]}

Zhou, Ling ^{[1
]}

机构：

[1] Northwest Univ, Dept Chem & Mat Sci, Minist Educ, Key Lab Synthet & Nat Funct Mol Chem, Xian 710127, Shaanxi, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 10期

基金：

中国国家自然科学基金;

关键词：

H INSERTION REACTIONS; LEWIS-ACID; ASYMMETRIC-SYNTHESIS; PROMOTED REACTIONS; BRONSTED ACID; O-HYDROXYSTYRENES; STYRENYL SYSTEMS; POVAROV REACTION; CONSTRUCTION; RESVERATROL;

D O I：

10.1021/acs.orglett.8b00988

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first highly enantioselective [3 + 2] formal cycloaddition of 1-styrylnaphthols (or phenol) with quinones catalyzed by a chiral phosphoric acid has been reported. A class of trans-2,3-diarylbenzofurans were prepared efficiently (up to 99% yield, >20:1 dr, 99% ee). This organocatalytic procedure allows lowering of the catalyst loading to 0.5 mol % without considerable loss in reactivity and enantioselectivity.

引用

页码：2929 / 2933

页数：5

共 50 条

[21] Enantioselective Bromocyclization of Olefins Catalyzed by Chiral Phosphoric Acid
Huang, Deshun
Wang, Haining
Xue, Fazhen
Guan, Huan
Li, Lijun
Peng, Xianyou
Shi, Yian
ORGANIC LETTERS, 2011, 13 (24) : 6350 - 6353
[22] Palladium-catalyzed diastereo- and enantioselective formal [3+2] cycloaddition of vinyl cyclopropanes with cyclic 1-azadienes
Zhou, Qing
Chen, Bo
Huang, Xiao-Bing
Zeng, Ya-Li
Chu, Wen-Dao
He, Long
Liu, Quan-Zhong
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (11) : 1891 - 1894
[23] Desymmetrization of Oxabenzonorbornadienes through Bronsted Acid-Catalyzed Enantioselective (3+2) Cycloaddition with Hydrazones
Prieto, Liher
Reyes, Efraim
Uria, Uxue
Carrillo, Luisa
Vicario, Jose L.
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (07)
[24] Formal oxo- and aza-[3+2] reactions of aenaminones and quinones: a double divergent process and the roles of chiral phosphoric acid and molecular sieves
Luo, Weiwei
Sun, Zhicheng
Fernando, E. H. Nisala
Nesterov, Vladimir N.
Cundari, Thomas R.
Wang, Hong
CHEMICAL SCIENCE, 2020, 11 (35) : 9386 - 9394
[25] Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid
Zhang, Minmin
Yu, Shuowen
Hu, Fangzhi
Liao, Yijun
Liao, Lihua
Xu, Xiaoying
Yuan, Weicheng
Zhang, Xiaomei
CHEMICAL COMMUNICATIONS, 2016, 52 (56) : 8757 - 8760
[26] Formal [3+2] cycloaddition of α-unsubstituted isocyanoacetates and methyleneindolinones: enantioselective synthesis of spirooxindoles
Peng, Xiao-Jiao
Ho, Yee Ann
Wang, Zhi-Peng
Shao, Pan-Lin
Zhao, Yu
He, Yun
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (01): : 81 - 85
[27] Bi(OAc)3/chiral phosphoric acid catalyzed enantioselective allylation of isatins
Wang, Jie
Zhang, Qingxia
Li, Yao
Liu, Xiangshuai
Li, Xin
Cheng, Jin-Pei
CHEMICAL COMMUNICATIONS, 2020, 56 (02) : 261 - 264
[28] Enantioselective synthesis of tetrahydroisoquinoline derivatives via chiral-at-metal rhodium complex catalyzed [3+2] cycloaddition
Qurban, Saira
Du, Yu
Gong, Jun
Lin, Shao-Xia
Kang, Qiang
CHEMICAL COMMUNICATIONS, 2019, 55 (02) : 249 - 252
[29] Asymmetric "Acetylenic" [3+2] Cycloaddition of Nitrones Catalyzed by Cationic Chiral PdII Lewis Acid
Honda, Kazuya
Mikami, Koichi
CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (19) : 2838 - 2841
[30] Chiral Phosphoric Acid Catalyzed Asymmetric Oxidative Dearomatization of Naphthols with Quinones
Zhu, Gongming
Bao, Guangjun
Li, Yiping
Yang, Junxian
Sun, Wangsheng
Li, Jing
Hong, Liang
Wang, Rui
ORGANIC LETTERS, 2016, 18 (20) : 5288 - 5291

← 1 2 3 4 5 →