A highly enantioselective four-component reaction for the efficient construction of chiral β-hydroxy-α-amino acid derivatives

被引：34

作者：

Qian, Yu ^{[1
]}

Jing, Changcheng ^{[1
]}

Liu, Shunying ^{[1
]}

Hu, Wenhao ^{[1
]}

机构：

[1] E China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Shanghai 200062, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 26期

基金：

美国国家科学基金会;

关键词：

MULTICOMPONENT REACTIONS AMCRS; DYNAMIC KINETIC RESOLUTION; BRONSTED ACID; INTRAMOLECULAR CYCLOPROPANATION; COOPERATIVE CATALYSIS; ASYMMETRIC-SYNTHESIS; THREONINE ALDOLASES; DIAZO-COMPOUNDS; ALDEHYDES; HYDROGENATION;

D O I：

10.1039/c3cc40546j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An enantioselective four-component reaction of a diazoketone, water, an aniline and ethyl glyoxylate in the presence of catalytic Rh-2(OAc)(4) and a chiral Bronsted acid was developed to efficiently produce beta-hydroxy-alpha-amino acid derivatives in good yields with high diastereoselectivity and enantioselectivity.

引用

页码：2700 / 2702

页数：3

共 50 条

[31] Four-Component Reaction for the Preparation of α-Amino Phosphonates from Methyleneaziridines
Mumford, Peter M.
Tarver, Gary J.
Shipman, Michael
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (09): : 3573 - 3575
[32] Siloxycyclopropanes in Ugi four-component reaction:: A new method for the synthesis of highly substituted pyrrolidinone derivatives
Zimmer, R
Ziemer, A
Gruner, M
Brüdgam, I
Hartl, H
Reissig, HU
SYNTHESIS-STUTTGART, 2001, (11): : 1649 - 1658
[33] Four-Component Reaction for Efficient Construction of Spiro[acenaphthylene-1,2-quinoline] skeleton
Zhu, Dan
Sun, Jing
Yan, Chao-Guo
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (02) : 583 - 587
[34] Enantioselective Construction of Amino Carboxylic-Phosphonic Acid Derivatives Enabled by Chiral Amino Thiourea-Catalyzed Decarboxylative Mannich Reaction
Wang, Xue-Qi
Feng, Fang-Fang
Nie, Jing
Zhang, Fa-Guang
Ma, Jun-An
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (11) : 1908 - 1912
[35] An efficient four-component reaction for the synthesis of chromeno[4,3-b]quinolone derivatives
Azadeh Yahya-Meymandi
Hamideh Nikookar
Setareh Moghimi
Mohammad Mahdavi
Loghman Firoozpour
Ali Asadipour
Parviz Rashidi Ranjbar
Alireza Foroumadi
Journal of the Iranian Chemical Society, 2017, 14 : 771 - 775
[36] The development of a catalytic synthesis of Munchnones:: A simple four-component coupling approach to α-amino acid derivatives
Dhawan, R
Dghaym, RD
Arndtsen, BA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (06) : 1474 - 1475
[37] An efficient four-component reaction for the synthesis of chromeno[4,3-b]quinolone derivatives
Yahya-Meymandi, Azadeh
Nikookar, Hamideh
Moghimi, Setareh
Mahdavi, Mohammad
Firoozpour, Loghman
Asadipour, Ali
Ranjbar, Parviz Rashidi
Foroumadi, Alireza
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2017, 14 (04) : 771 - 775
[38] Highly diastereoselective epimerization:: Stereodivergent synthesis of α-hydroxy-β-amino isopentanoic acid
Seo, Woo Duck
Curtis-Long, Marcus J.
Ryu, Young Bae
Lee, Jin Hwan
Yang, Min Suk
Lee, Woo Song
Park, Ki Hun
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13): : 5008 - 5011
[39] A simple and efficient approach to the synthesis of furopyran derivatives: four-component reaction of isocyanides with arylidene-substituted Meldrum’s acid
A. Habibi
E. Sheikhhosseini
N. Taghipoor
Chemistry of Heterocyclic Compounds, 2013, 49 : 968 - 973
[40] Copper-Catalyzed Asymmetric Hydroboration of α-Dehydroamino Acid Derivatives: Facile Synthesis of Chiral β-Hydroxy-α-amino Acids
He, Zhi-Tao
Zhao, Yi-Shuang
Tian, Ping
Wang, Chuan-Chuan
Dong, Han-Qing
Lin, Guo-Qiang
ORGANIC LETTERS, 2014, 16 (05) : 1426 - 1429

← 1 2 3 4 5 →