Bifunctional thiourea-promoted cascade aza-Michael-Henry-dehydration reactions: asymmetric preparation of 3-nitro-1,2-dihydroquinolines

被引：52

作者：

Liu, Xiaoqian

Lu, Yixin ^{[1
]}

机构：

[1] Natl Univ Singapore, Inst Life Sci, Dept Chem, Singapore 117548, Singapore

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 18期

关键词：

ENANTIOSELECTIVE CONJUGATE ADDITION; RECENT PROGRESS; NITRO-OLEFINS; NITROALKENES; MALONATE; DERIVATIVES; CATALYSIS; ALDEHYDES; ACID;

D O I：

10.1039/c0ob00223b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A cascade aza-Michael-Henry-dehydration reaction catalyzed by quinidine-derived tertiary amine-thiourea catalyst was developed via installation of suitable electron withdrawing groups at the amino function of aniline. This strategy led to a one-step preparation of chiral 3-nitro-1,2-dihydroquinolines in high yields and with up to 90% enantiomeric excesses.

引用

页码：4063 / 4065

页数：3

共 4 条

[1] Enantioselective Catalytic Domino Aza-Michael-Henry Reactions: One-Pot Asymmetric Synthesis of 3-Nitro-1,2-dihydroquinolines via Iminium Activation
Luo, Hao
Yan, Xilong
Chen, Ligong
Li, Yang
Liu, Na
Yin, Guohui
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (09) : 1702 - 1707
[2] One-Pot Organocatalytic Asymmetric Synthesis of 3-Nitro-1,2-dihydroquinolines by a Dual-Activation Protocol
Wang, Yi-Feng
Zhang, Wei
Luo, Shu-Ping
Li, Bai-Lin
Xia, Ai-Bao
Zhong, Ai-Guo
Xu, Dan-Qian
CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (12) : 1834 - 1838
[3] Heterogeneous Synergistic Catalysis for Promoting Aza-Michael-Henry Tandem Reaction for the Synthesis of Chiral 3-Nitro-1,2-Dihydroquinoline
An, Zhe
Chen, Lifeng
Jiang, Yitao
He, Jing
CATALYSTS, 2019, 9 (09)
[4] N-Heterocyclic Carbene-Catalyzed Kinetic Resolution of 3-Nitro-1,2-Dihydroquinolines: Asymmetric Synthesis of All C2-, C3- and C4-Functionalized Tetrahydroquinolines
Shukla, Pushpendra Mani
Pratap, Aniruddh
Maji, Biswajit
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (17)

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