A Versatile Synthesis of Various Substituted Taurines from Vicinal Amino Alcohols and Aziridines

被引：50

作者：

Chen, Ning ^{[1
]}

Jia, Weiyi ^{[1
]}

Xu, Jiaxi ^{[1
]}

机构：

[1] Beijing Univ Chem Technol, State Key Lab Chem Resource Engn, Dept Organ Chem, Fac Sci, Beijing 100029, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 33期

基金：

北京市自然科学基金; 中国国家自然科学基金;

关键词：

Synthetic methods; Amino acids; Amino alcohols; Heterocycles; Sulfonic acids; ASYMMETRIC-SYNTHESIS; CYCLOHEXYL SULFONATES; CARBON-DISULFIDE; ACID; ANALOGS; SULFINAMIDE; PEPTIDES;

D O I：

10.1002/ejoc.200900759

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Taurine and structurally diverse substituted taurines have been synthesized by peroxyformic acid oxidation of the thiazolidine-2-thione intermediates generated from vicinal amino alcohols or aziridines and carbon disulfide. The stereochemistry and mechanisms of the reactions are disscussed. The method is a salt-free and versatile route, convenient in terms of purification, and can be used to synthesize optically active substituted taurines. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：5841 / 5846

页数：6

共 58 条

[1] Synthesis and pyrolytic behaviour of thiazolidin-2-one 1,1-dioxides [J].

Aitken, RA ;

Armstrong, DP ;

Galt, RHB ;

Mesher, STE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (14) :2139-2145

[2] Synthesis and biological evaluation of thiazolidine-2-one 1,1-dioxide as inhibitors of Escherichia coli β-ketoacyl-ACP-synthase III (FabH) [J].

Alhamadsheh, Mamoun M. ;

Waters, Norman C. ;

Huddler, Donald P. ;

Kreishman-Deitrick, Mara ;

Florova, Galina ;

Reynolds, Kevin A. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (04) :879-883

[3]

[Anonymous], B SOC CHIM FR

[4] Analogues of pantothenic acid - Part IV Aryl derivatives of pantoyltaurine [J].

Barnett, J ;

Dupre, DJ ;

Holloway, BJ ;

Robinson, FA .

JOURNAL OF THE CHEMICAL SOCIETY, 1944, :94-96

[5] SYNTHESIS AND CHEMISTRY OF S-ACYLTHIOL S-OXIDES AND RELATED COMPOUNDS [J].

BARTON, DHR ;

MANLY, DP ;

WIDDOWSON, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1568-1574

[6] Asymmetric synthesis of (R)- and (S)-2-pyrrolidinemethanesulfonic acid [J].

Braghiroli, D ;

Avallone, R ;

DiBella, M .

TETRAHEDRON-ASYMMETRY, 1997, 8 (13) :2209-2213

[7] Asymmetric synthesis of 2-methyltaurine [J].

Braghiroli, D ;

Mussati, E ;

DiBella, M ;

Saladini, M .

TETRAHEDRON-ASYMMETRY, 1996, 7 (03) :831-836

[8] Synthesis of gem-disubstituted taurines by the regioselective ring-opening of 2,2-disubstituted aziridines with sodium bisulfite and sulfite [J].

Chen, Ning ;

Zhu, Min ;

Zhang, Wei ;

Du, Da-Ming ;

Xu, Jiaxi .

AMINO ACIDS, 2009, 37 (02) :309-313

[9]

Cordero FM, 2002, EUR J ORG CHEM, V2002, P1407, DOI 10.1002/1099-0690(200204)2002:8<1407::AID-EJOC1407>3.0.CO

[10]

2-I

← 1 2 3 4 5 6 →