Asymmetric α-Amination of 4-Substituted Pyrazolones Catalyzed by a Chiral Gd(OTf)3/N,N′-Dioxide Complex: Highly Enantioselective Synthesis of 4-Amino-5-pyrazolone Derivatives

被引：119

作者：

Yang, Zhigang ^{[1
]}

Wang, Zhen ^{[1
]}

Bai, Sha ^{[1
]}

Liu, Xiaohua ^{[1
]}

Lin, Lili ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 04期

基金：

中国国家自然科学基金;

关键词：

FRIEDEL-CRAFTS ALKYLATION; BETA-KETO-ESTERS; MICHAEL ADDITION; QUATERNARY STEREOCENTERS; CARBONYL-COMPOUNDS; ALDEHYDES; CONSTRUCTION; ACID; HYDROXYMETHYLATION; CYANOACETATES;

D O I：

10.1021/ol102804p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric alpha-amination of 4-substituted pyrazolones with azodicarboxylates was investigated for the first time, employing an N,N'-dioxide gadolinium(III) complex as the catalyst. The novel transformations exhibited high yield, and 4-amino-5-pyrazolone derivatives bearing a chiral quaternary center were obtained in excellent yields (up to 99%) and enantioselectivities (90%-97% ee) for a broad scope of 5-pyrazolones by using 1 mol A or only 0.05 mol % of catalyst.

引用

页码：596 / 599

页数：4

共 50 条

[41] SYNTHESIS & ANTI-MICROBIAL EVALUATION OF N-(2-(4-SUBSTITUTED PHENYL)-4-OXOTHIAZOLIDIN-3-YL) ISONICOTINAMIDE DERIVATIVES
Ramachandran, S.
Shanmugapandiyan, P.
Nalini, C. N.
[J]. INTERNATIONAL JOURNAL OF PHARMACEUTICAL SCIENCES AND RESEARCH, 2011, 2 (06): : 1564 - 1568
[42] SYNTHESIS OF 3' -FLUORO AND 3',5' -DIFLUORO DERIVATIVES OF 4-AMINO-4-DEOXY-N10-METHYLPTEROYLGLUTAMIC ACID (METHOTREXATE)
TOMCUFCIK, A
SEEGER, DR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (09): : 3351 - &
[43] POTENTIAL ANALGESICS .8. SYNTHESIS AND PHARMACOLOGICAL TEST OF 3-SUBSTITUTED, 4-SUBSTITUTED AND 5-SUBSTITUTED N-ARYLANTHRANILIC ACIDS
BURKARTSMAIER, A
MUTSCHLER, E
[J]. ARCHIV DER PHARMAZIE, 1978, 311 (02) : 161 - 170
[44] Synthesis and Biological Activity of N-[3-(4-Substituted Phenyl)-3-hydroxypropyl]valines and -Tryptophans, and 3-{[3-Hydroxy-3-(4-substituted phenyl)propyl]amino}-3-phenylpropanoic Acids
A. G. Agababyan
G. A. Gevorgyan
A. P. Avakyan
A. E. Tumadzhyan
R. G. Paronikyan
G. A. Panosyan
[J]. Pharmaceutical Chemistry Journal, 2013, 47 : 361 - 365
[45] Chiral Cu(II)-N4 Complex Catalyzed Asymmetric Aza-Henry Reaction and Its Application in the Synthesis of β-Diamine
Menapara, Tusharkumar
Tak, Rajkumar
Chinnaraja, E.
Kureshy, Rukhsana I.
Patel, Parth
Khan, Noor-ul H.
[J]. CHEMISTRYSELECT, 2017, 2 (14): : 4063 - 4067
[46] SYNTHESIS AND BIOLOGICAL ACTIVITY OF N-[3-(4-SUBSTITUTED PHENYL)-3-HYDROXYPROPYL]VALINES AND -TRYPTOPHANS, AND 3-{[3-HYDROXY-3-(4-SUBSTITUTED PHENYL)PROPYL]AMINO}-3-PHENYLPROPANOIC ACIDS
Agababyan, A. G.
Gevorgyan, G. A.
Avakyan, A. P.
Tumadzhyan, A. E.
Paronikyan, R. G.
Panosyan, G. A.
[J]. PHARMACEUTICAL CHEMISTRY JOURNAL, 2013, 47 (07) : 361 - 365
[47] Asymmetric Allylation of -Ketoester-Derived N-Benzoylhydrazones Promoted by Chiral Sulfoxides/N-Oxides Lewis Bases: Highly Enantioselective Synthesis of Quaternary -Substituted -Allyl--Amino Acids
Reyes-Rangel, Gloria
Bandala, Yamir
Garcia-Flores, Fred
Juaristi, Eusebio
[J]. CHIRALITY, 2013, 25 (09) : 529 - 540
[48] Synthesis, structural and spectroscopic studies of 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone N(4)-methyl-N(4)-phenyl thiosemicarbazone and its cadmium(II) complex
Sangeetha, K. G.
Aravindakshan, K. K.
[J]. INORGANICA CHIMICA ACTA, 2018, 469 : 25 - 31
[49] A convergent microwave assisted synthesis of 4-amino-N-(4-oxo2-substituted-4H-quinazolin-3-yl)benzenesulfonamide derivatives
Jagani, Chandresh L.
Sojitra, Natvar A.
Vanparia, Satish F.
Patel, Tarosh S.
Dixit, Ritu B.
Dixit, Bharat C.
[J]. ARKIVOC, 2011, : 221 - +
[50] Synthesis of N-substituted derivatives of 5(4)-[bis(2-chlorethyl)amino]-4(5)-nitroimidazole being new group of anticancer drugs.
Weidlich, I
Sobiak, S
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U54 - U54

← 1 2 3 4 5 →