Remote stereocontrolled asymmetric 1,6-addition/1,4-addition cascade reactions between cyclic dienones and 2-indolinethiones

被引：17

作者：

Sun, Xiaohua ^{[1
]}

Fei, Jie ^{[1
]}

Zou, Chuncheng ^{[1
]}

Lu, Min ^{[1
]}

Ye, Jinxing ^{[1
]}

机构：

[1] East China Univ Sci & Technol, Minist Educ, Shanghai Key Lab New Drug Design, Engn Res Ctr Pharmaceut Proc Chem,Sch Pharm, 130 Meilong Rd, Shanghai 200237, Peoples R China

来源：

RSC ADVANCES | 2016年 / 6卷 / 108期

基金：

中国国家自然科学基金;

关键词：

SULFA-MICHAEL ADDITION; ALPHA; BETA-UNSATURATED KETONES; ENANTIOSELECTIVE CONSTRUCTION; ORGANOCASCADE CATALYSIS; VINYL KETONES; PRIMARY AMINE; SPIROOXINDOLES; ACTIVATION; ENONES; FUNCTIONALIZATION;

D O I：

10.1039/c6ra19916j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly enantioselective 1,6-addition/1,4-addition cascade reactions between cyclic dienones and 2-indolnethiones have been realized by employing a cinchona-based primary amine catalyst. This method displays a broad substrate scope and provides a simple and highly effective way to achieve the chiral spiro[thiopyranoindole-cyclohexanone] scaffold.

引用

页码：106676 / 106679

页数：4

共 50 条

[1] Organocatalytic 1,4-Addition Reaction of α,β-γ,δ-Diunsaturated Aldehydes versus 1,6-Addition Reaction
Hayashi, Yujiro
Okamura, Daichi
Umemiya, Shigenobu
Uchimaru, Tadafumi
CHEMCATCHEM, 2012, 4 (07) : 959 - 962
[2] Aminocatalytic Enantioselective 1, 6-Addition of (Nitromethyl)benzenes to α, β, γ, δ-Cyclic Dienones
Feng, Kai-Xiang
Shen, Qiao-Yu
Zheng, Ya-Yun
Xia, Ai-Bao
Zhou, Zhan-Yu
Tang, Cheng-Ke
Zhong, Ai-Guo
Xu, Dan-Qian
Du, Xiao-Hua
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (39) : 6626 - 6630
[3] Catalytic Asymmetric 1,4-Addition Reactions of Simple Alkylnitriles
Yamashita, Yasuhiro
Sato, Io
Suzuki, Hirotsugu
Kobayashi, Shu
CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (10) : 2143 - 2146
[4] Advances in Organocatalytic 1,6-Addition Reactions: Enantioselective Construction of Remote Stereogenic Centers
Chauhan, Pankaj
Kaya, Ugur
Enders, Dieter
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (06) : 888 - 912
[5] Recent topics on catalytic asymmetric 1,4-addition
Hayashi, Masahiko
Matsubara, Ryosuke
TETRAHEDRON LETTERS, 2017, 58 (19) : 1793 - 1805
[6] Catalytic asymmetric direct-type 1,4-addition reactions of simple esters
Sato, Io
Suzuki, Hirotsugu
Yamashita, Yasuhiro
Kobayashi, Shu
ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (10): : 1241 - 1245
[7] Remote Construction of Chiral Vicinal Tertiary and Quaternary Centers by Catalytic Asymmetric 1,6-Conjugate Addition of Prochiral Carbon Nucleophiles to Cyclic Dienones
Wei, Yuan
Liu, Zunwu
Wu, Xinxin
Fei, Jie
Gu, Xiaodong
Yuan, Xiaoqian
Ye, Jinxing
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (52) : 18921 - 18924
[8] Cobalt-Catalyzed Asymmetric 1,6-Addition of (Triisopropylsilyl)-acetylene to α,β,γ,δ-Unsaturated Carbonyl Compounds
Sawano, Takahiro
Ashouri, Akram
Nishimura, Takahiro
Hayashi, Tamio
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (46) : 18936 - 18939
[9] Asymmetric 1,4-Addition of Diarylphosphine Oxides to α, β-Unsaturated 2-Acyl Imidazoles
Chen, Lirong
Wang, Guiyong
Nong, Xiufei
Shao, Wendi
Li, Jiuling
Guo, Yafei
Fan, Baomin
CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (36)
[10] Palladium-Catalyzed Asymmetric 1,4-Addition of Diarylphosphines to α,β-Unsaturated Sulfonyl Fluorides
Cheng, An-Qi
Wu, Zeng-Hua
Yang, Huai-Lan
Duan, Wei-Liang
SYNTHESIS-STUTTGART, 2023, 55 (17): : 2773 - 2778

← 1 2 3 4 5 →