Chiral NHC Ligands Bearing a Pyridine Moiety in Copper-Catalyzed 1,2-Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated N-Tosylaldimines

被引：12

作者：

Soeta, Takahiro ^{[1
]}

Ishizaka, Tomohiro ^{[1
]}

Ukaji, Yutaka ^{[1
]}

机构：

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Mat Chem, Kanazawa, Ishikawa 9201192, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 07期

基金：

日本学术振兴会;

关键词：

ASYMMETRIC ALLYLIC SUBSTITUTION; HETEROCYCLIC CARBENE LIGANDS; LITHIUM ESTER ENOLATE; CONJUGATE ADDITION; ENANTIOSELECTIVE SYNTHESIS; ALLYLAMINE DERIVATIVES; TERNARY COMPLEX; IMINES; ALKYLATION; ARYLATION;

D O I：

10.1021/acs.joc.6b00093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric 1,2-addition of dialkylzinc reagents to alpha,beta-unsaturated N-tosylaldimines was catalyzed by copper salt in the presence of chiral imidazolium salts having a pyridine ring, which were derived from amino acid, to afford the corresponding chiral allylic amines with up to 91% ee in reasonably high yields. The chiral N-heterocyclic carbene (NHC) ligand played an important role in controlling chemoselectivity.

引用

页码：2817 / 2826

页数：10

共 17 条

[1] Chiral NHC ligands bearing a pyridine moiety in copper-catalyzed addition of diethylzinc to nitroalkenes
Soeta, Takahiro
Hatanaka, Yuichi
Ishizaka, Tomohiro
Ukaji, Yutaka
TETRAHEDRON, 2018, 74 (35) : 4601 - 4605
[2] Chiral N-Heterocyclic Carbene Ligands Bearing a Pyridine Moiety for the Copper-Catalyzed Alkylation of N-Sulfonylimines with Dialkylzinc Reagents
Soeta, Takahiro
Ishizaka, Tomohiro
Tabatake, Yuta
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CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (50) : 16773 - 16778
[3] Chiral NHC Ligands for the Copper-Catalyzed Asymmetric Conjugate Addition of Grignard Reagents
Germain, Nicolas
Magrez, Magaly
Kehrli, Stefan
Mauduit, Marc
Alexakis, Alexandre
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (27) : 5301 - 5306
[4] Copper-catalyzed enantioselective 1,4-conjugate addition of dialkylzinc reagents to α,β- and α,β,γ,δ-unsaturated ketones
Rexiti, Rukeya
Lu, Jian
Sha, Feng
Wu, Xin-Yan
TETRAHEDRON, 2019, 75 (26) : 3596 - 3604
[5] Copper-Catalyzed Chemoselective and Enantioselective Friedel Crafts 1,2-Addition of Pyrrole with β,γ-Unsaturated α-Ketoesters
Sun, Jianan
Hu, Yanbin
Li, Yanan
Zhang, Sheng
Zha, Zhenggen
Wang, Zhiyong
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (10): : 5102 - 5110
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Madduri, Ashoka V. R.
Minnaard, Adriaan J.
Harutyunyan, Syuzanna R.
CHEMICAL COMMUNICATIONS, 2012, 48 (10) : 1478 - 1480
[7] Palladium-catalyzed 1,2-addition of potassium aryl- and alkenyltrifluoroborates to aldehydes using thioether-imidazolinium carbene ligands
Kuriyama, Masami
Shimazawa, Rumiko
Enomoto, Terumichi
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JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17): : 6939 - 6942
[8] Copper-Catalyzed Asymmetric 1,2-Addition of Grignard Reagents to 3-Acyl 2H-chromenes
Calvo, Beatriz C.
Minnaard, Adriaan J.
SYNLETT, 2017, 28 (19) : 2624 - 2628
[9] Electronic tuning of chiral diene ligands in iridium-catalyzed asymmetric 1,6-addition of arylboroxines to δ-aryl-α,β,γ,δ-unsaturated ketones
Nishimura, Takahiro
Noishiki, Akira
Hayashi, Tamio
CHEMICAL COMMUNICATIONS, 2012, 48 (07) : 973 - 975
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Knobel, AKH
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SYNLETT, 1997, (12) : 1429 - 1431

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