Asymmetric Michael reactions of α,α-disubstituted aldehydes with maleimides using a primary amine thiourea organocatalyst

被引：42

作者：

Miura, Tsuyoshi ^{[1
]}

Masuda, Akira ^{[1
]}

Ina, Mariko ^{[1
]}

Nakashima, Kosuke ^{[1
]}

Nishida, Shohei ^{[1
]}

Tada, Norihiro ^{[1
]}

Itoh, Akichika ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Gifu 5011196, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 16-17期

基金：

日本学术振兴会;

关键词：

ENANTIOSELECTIVE CONJUGATE ADDITION; ALDOL REACTIONS; GUANIDINE;

D O I：

10.1016/j.tetasy.2011.09.006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Primary amine thiourea organocatalyst 8 was used to promote Michael additions of bulky alpha,alpha-disubstituted aldehydes, such as isobutyraldehyde with maleimides to afford the corresponding adducts in high to excellent yields and with up to 91% ee. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：1605 / 1609

页数：5

共 50 条

[41] Pyrrolidine-oxyimide catalyzed asymmetric Michael addition of α,α-disubstituted aldehydes to nitroolefins
Kumar, Togapur Pavan
TETRAHEDRON-ASYMMETRY, 2015, 26 (17) : 907 - 911
[42] Asymmetric Michael Addition of γ,γ-Disubstituted α,β-Unsaturated Aldehydes to Nitroolefins via Dienamine Catalysis
Han, Bo
Xiao, You-Cai
He, Zhao-Quan
Chen, Ying-Chun
ORGANIC LETTERS, 2009, 11 (20) : 4660 - 4663
[43] An amine sulfonamide organocatalyst for promoting direct, highly enantioselective α-aminoxylation reactions of aldehydes and ketones
Wang, W
Wang, J
Li, H
Liao, LX
TETRAHEDRON LETTERS, 2004, 45 (39) : 7235 - 7238
[44] Optically active helical polymers with pendent thiourea groups: Chiral organocatalyst for asymmetric michael addition reaction
Zhang, Haiyang
Yang, Wantai
Deng, Jianping
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2015, 53 (15) : 1816 - 1823
[45] Asymmetric Henry Reactions of Aldehydes Using Chiral Biaryl-Based Bis(thiourea) Organocatalysts
Nakayama, Yuki
Hidaka, Yusaku
Ito, Katsuji
SYNLETT, 2013, 24 (07) : 883 - 885
[46] Hybrid Peptide-Thiourea Catalyst for Asymmetric Michael Additions of Aldehydes to Heterocyclic Nitroalkenes
Cmelova, Patricia
Vargova, Denisa
Sebesta, Radovan
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 581 - 592
[47] Asymmetric Michael addition of aldehydes to nitroalkenes using a primary amino acid lithium salt
Yoshida, Masanori
Sato, Atsushi
Hara, Shoji
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (13) : 3031 - 3036
[48] Asymmetric conjugate addition of aldehydes to vinyl sulfone using a diaminomethylenemalononitrile organocatalyst
Kanada, Yohei
Yuasa, Hiroki
Nakashima, Kosuke
Murahashi, Miho
Tada, Norihiro
Itoh, Akichika
Koseki, Yuji
Miura, Tsuyoshi
TETRAHEDRON LETTERS, 2013, 54 (36) : 4896 - 4899
[49] Diarylprolinol as an Effective Organocatalyst in Asymmetric Cross-aldol Reactions of Two Different Aldehydes
Hayashi, Yujiro
CHEMICAL RECORD, 2023, 23 (07):
[50] C2-Symmetric Chiral Squaramide, Recyclable Organocatalyst for Asymmetric Michael Reactions
Kucherenko, Alexander S.
Kostenko, Alexey A.
Komogortsev, Andrey N.
Lichitsky, Boris V.
Fedotov, Michael Yu.
Zlotin, Sergei G.
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (07): : 4304 - 4311

← 1 2 3 4 5 →