Pd-Catalyzed Diastereo- and Enantioselective [3+2]-Cycloaddition Reaction of Vinyl Epoxide with Nitroalkenes

被引：43

作者：

Wu, Wen-Qiong ^{[1
]}

Ding, Chang-Hua ^{[2
]}

Hou, Xue-Long ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai Hong Kong Joint Lab Chem Synth, Shanghai 200032, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

SYNLETT | 2012年 / 07期

基金：

中国国家自然科学基金;

关键词：

vinyl epoxide; nitroalkene; palladium; asymmetric catalysis; 3+2] cycloaddition; ASYMMETRIC CYCLOADDITION REACTIONS; SATURATED OXYGEN HETEROCYCLES; ACTIVATED OLEFINS; HECK REACTION; CASCADE REACTIONS; LIGANDS; TETRAHYDROFURANS; VINYLAZIRIDINES; CYCLOPROPANES; DERIVATIVES;

D O I：

10.1055/s-0031-1290525

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A diastereoselective and enantioselective [3+2]-cycloaddition reaction of vinyl epoxide and nitroalkenes has been developed using Pd/1,1'-ferrocene-P, N-ligand, providing substituted tetrahydrofurans in high yields and with high diastereo- and enantioselectivities.

引用

页码：1035 / 1038

页数：4

共 50 条

[1] Pd-Catalyzed Regio-, Diastereo-, and Enantioselective [3+2] Cycloaddition Reactions: Access to Chiral Cyclopentyl Sulfones
Trost, Barry M.
Zhu, Chuanle
Ence, Chloe Christine
[J]. ORGANIC LETTERS, 2021, 23 (07) : 2460 - 2464
[2] Highly Diastereo- and Enantioselective Palladium-Catalyzed [3+2] Cycloaddition of Vinyl Aziridines and α,β-Unsaturated Ketones
Xu, Chao-Fan
Zheng, Bao-Hui
Suo, Jia-Jia
Ding, Chang-Hua
Hou, Xue-Long
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (05) : 1604 - 1607
[3] Highly Diastereo- and Enantioselective Palladium-Catalyzed [3+2] Cycloaddition of Vinyl Epoxides and α,β-Unsaturated Ketones
Suo, Jia-Jia
Du, Juan
Liu, Qing-Rong
Chen, Di
Ding, Chang-Hua
Peng, Qian
Hou, Xue-Long
[J]. ORGANIC LETTERS, 2017, 19 (24) : 6658 - 6661
[4] Electron-Deficient Alkynes as Dipolarophile in Pd-Catalyzed Enantioselective (3+2) Cycloaddition Reaction with Vinyl Cyclopropanes
Ding, Wen-Ping
Zhang, Gao-Peng
Jiang, Yang-Jie
Du, Juan
Liu, Xiu-Yan
Chen, Di
Ding, Chang-Hua
Deng, Qing-Hai
Hou, Xue-Long
[J]. ORGANIC LETTERS, 2019, 21 (17) : 6805 - 6810
[5] Diastereo- and Enantioselective Palladium-Catalyzed Dearomative [3+2] Cycloaddition of 3-Nitroindoles
Suo, Jia-Jia
Liu, Wei
Du, Juan
Ding, Chang-Hua
Hou, Xue-Long
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (08) : 959 - 963
[6] 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
[J]. ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (11) : 1891 - 1894
[7] Pd-catalyzed [3+2] cycloaddition reaction of carbon dioxide
Greco, GE
Gleason, BL
Lowery, TA
Kier, MJ
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3247 - U3248
[8] Zn-Catalyzed Diastereo- and Enantioselective Dearomative [3+2] Cycloaddition Reaction of 2-Nitroindoles and 2-Nitrobenzothiophenes
Zhao, Jian-Qiang
Zhou, Xiao-Jian
Chen, Yong-Zheng
Xu, Xiao-Ying
Zhang, Xiao-Mei
Yuan, Wei-Cheng
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (13) : 2482 - 2487
[9] Pd-Catalyzed Enantioselective (3+2)-Cycloaddition of Vinyl-Substituted Oxyallyl Carbonates with Isocyanates and Ketones
Pan, Xuemei
Yu, Limei
Wang, Simin
Wu, Rui
Ou, Chunyan
Xu, Minghui
Chen, Bin
Gao, Yuanji
Ni, Hai-Liang
Hu, Ping
Wang, Bi-Qin
Cao, Peng
[J]. ORGANIC LETTERS, 2022, 24 (11) : 2099 - 2103
[10] Diastereo- and Enantioselective Dearomative [3+2] Cycloaddition Reaction of 2-Nitrobenzofurans with 3-Isothiocyanato Oxindoles
Zhao, Jian-Qiang
Zhou, Xiao-Jian
Zhou, Yan
Xu, Xiao-Ying
Zhang, Xiao-Mei
Yuan, Wei-Cheng
[J]. ORGANIC LETTERS, 2018, 20 (04) : 909 - 912

← 1 2 3 4 5 →