Enantioselective copper(II)-catalyzed Henry reaction utilizing chiral aziridinyl alcohols

被引：10

作者：

Wang, Xiaojuan ^{[1
]}

Zhao, Wenxian ^{[1
,2
]}

Li, Gaowei ^{[1
]}

Wang, Jin ^{[2
]}

Liu, Guanjun ^{[2
]}

Liu, Lantao ^{[1
]}

Zhao, Ruijuan ^{[2
]}

Wang, Mincan ^{[2
]}

机构：

[1] Shangqiu Normal Univ, Sch Chem & Chem Engn, Shangqiu 476000, Henan, Peoples R China

[2] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450052, Henan, Peoples R China

来源：

APPLIED ORGANOMETALLIC CHEMISTRY | 2014年 / 28卷 / 12期

基金：

中国国家自然科学基金;

关键词：

aziridinyl alcohols; copper; asymmetric synthesis; Henry reaction; ASYMMETRIC NITROALDOL REACTION; AMINO-ALCOHOLS; LIGANDS; ALDEHYDES; DIETHYLZINC; CATALYST; COMPLEX; REDUCTION; DESIGN;

D O I：

10.1002/aoc.3232

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A family of enantiopure -aminoalcohols based on aziridine backbones were synthesized, and examined as chiral ligands for the copper(II)-catalyzed asymmetric Henry reaction of aromatic aldehydes with nitromethane, giving -nitroalcohols in excellent yields (up to 93%) and moderate to good enantioselectivities (up to 82%). Moreover, possible transition states of the reaction are proposed. Copyright (c) 2014 John Wiley & Sons, Ltd.

引用

页码：892 / 899

页数：8

共 50 条

[31] Chiral 2-endo-Substituted 9-Oxabispidines: Novel Ligands for Enantioselective Copper(II)-Catalyzed Henry Reactions
Breuning, Matthias
Hein, David
Steiner, Melanie
Gessner, Viktoria H.
Strohmann, Carsten
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (46) : 12764 - 12769
[32] Enantioselective acylations of alcohols catalyzed by chiral phosphines.
Daugulis, O
Vedejs, E
Diver, ST
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 444 - ORGN
[33] Enantioselective Cu(II)-catalyzed Henry reactions with chiral cyclohexane-based amidophosphine ligands
Rexiti, Rukeya
Lu, Jian
Wang, Ge
Sha, Feng
Wu, Xin-Yan
TETRAHEDRON-ASYMMETRY, 2016, 27 (19) : 923 - 929
[34] Copper complex of phenylglycine-functionalized <bold/>: a chiral MOF catalyst for enantioselective Henry reaction
Rasolinia, Khadijeh
Arvinnezhad, Hamid
Samadi, Saadi
NEW JOURNAL OF CHEMISTRY, 2024, 49 (01) : 213 - 222
[35] New Adaptive Chiral Thiophene Ligands for Copper-Catalyzed Asymmetric Henry Reaction
Bandini, Marco
Cabiddu, Salvatore
Cadoni, Enzo
Olivelli, Pasquale
Sinisi, Riccardo
Umani-Ronchi, Achille
Usai, Michele
CHIRALITY, 2009, 21 (01) : 239 - 244
[36] Copper-Chiral Camphor -Amino Alcohol Complex Catalyzed Asymmetric Henry Reaction
Xu, Feng
Lei, Chao
Yan, Lei
Tu, Jingxuan
Li, Gaoqiang
CHIRALITY, 2015, 27 (10) : 761 - 765
[37] Chiral N-arylated diamine - Copper complexes catalyzed asymmetric Henry reaction
El-Asaad, Bilal
Metay, Estelle
Karame, Iyad
Lemaire, Marc
MOLECULAR CATALYSIS, 2017, 435 : 76 - 81
[38] Enantioselective Henry Reaction Catalyzed by Copper(II) Complex of Bis(trans-cyclohexane-1,2-diamine)-Based Ligand
Tetour, David
Novotna, Marika
Hodacova, Jana
CATALYSTS, 2021, 11 (01) : 1 - 10
[39] Enantioselective Henry Reaction Catalyzed by "Ship in a Bottle" Complexes
Bania, Kusum K.
Karunakar, Galla V.
Goutham, Kommuru
Deka, Ramesh C.
INORGANIC CHEMISTRY, 2013, 52 (14) : 8017 - 8029
[40] Asymmetric Henry reaction catalyzed by a copper tridentate chiral schiff-base complex
Lai, Guoyin
Wang, Sujing
Wang, Zhiyong
TETRAHEDRON-ASYMMETRY, 2008, 19 (15) : 1813 - 1819

← 1 2 3 4 5 →