An efficient synthesis of aziridines from ephedrines

被引：5

作者：

Cruz, Alejandro ^{[1
]}

Irene Padilla-Martinez, Itzia ^{[1
]}

Garcia-Baez, Efren V. ^{[1
]}

机构：

[1] IPN, Dept Ciencias Basicas, Unidad Profes Interdisciplinaria Biotecnol, Mexico City 07340, DF, Mexico

来源：

TETRAHEDRON-ASYMMETRY | 2010年 / 21卷 / 08期

关键词：

ASYMMETRIC TRANSFER HYDROGENATION; ONE-POT SYNTHESIS; CHIRAL AUXILIARY; ENANTIOSELECTIVE ADDITION; DIETHYLZINC; LIGANDS; ALCOHOLS; (S; S)-(+)-PSEUDOEPHEDRINE; PSEUDOEPHEDRINE; ALDEHYDES;

D O I：

10.1016/j.tetasy.2010.05.007

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The reaction of chlorodeoxyephedrine hydrochlorides with one, two, and three molar equivalents of base was studied. Isochlorodeoxypseudoepherines were identified and assigned by H-1 and C-13 NMR data as intermediate compounds in the formation of cis-aziridines. Erythro and threo ephedrinethylethers were isolated as new compounds and analyzed by spectroscopic data. In addition, the erythro isomer was studied by X-ray diffraction. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：909 / 913

页数：5

共 49 条

[11] 1,3-heterazolidin-2-ones as starting materials for optically active 1,3,2-oxazaborolines and 1,3,2-diazaboroline derived from ephedrines [J].

Cruz, A ;

Geníz, E ;

Contreras, R .

TETRAHEDRON-ASYMMETRY, 1998, 9 (22) :3991-3996

[12] Synthesis of optically active boroxazolidine, borathiazolidine and boraselenazolidine and their N-borane adducts from the corresponding 2-imino-heteroazolidines [J].

Cruz, A ;

Macías-Mendoza, D ;

Barragan-Rodríguez, E ;

Tlahuext, H ;

Nöth, H ;

Contreras, R .

TETRAHEDRON-ASYMMETRY, 1997, 8 (23) :3903-3911

[13] THIAZABOROLIDINES AND BH3 ADDUCTS DERIVED FROM THIOEPHEDRINES [J].

CRUZ, A ;

FLORESPARRA, A ;

TLAHUEXT, H ;

CONTRERAS, R .

TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :1933-1940

[14] Reactivity of chlorodeoxypseudoephedrines with oxo-, thio-, and selenocyanates [J].

Cruz, Alejandro ;

Padilla-Martinez, Itzia Irene ;

Garcia-Baez, Efren V. ;

Contreras, Rosalinda .

TETRAHEDRON-ASYMMETRY, 2007, 18 (01) :123-130

[15] 1,3-heterazolidines-2-heterounsaturated compounds derived from ephedrines [J].

Cruz, Alejandro ;

Contreras, Rosalinda ;

Padilla-Martinez, Itzia I. ;

Juarez-Juarez, Minerva .

TETRAHEDRON-ASYMMETRY, 2006, 17 (10) :1499-1505

[16]

DESOUSA SE, 1998, J CHEM SOC P1, V1483, P1492

[17] STEREOSELECTIVE AND REGIOSELECTIVE SYNTHESIS OF CHIRAL DIAMINES AND TRIAMINES FROM PSEUDOEPHEDRINE AND EPHEDRINE [J].

DIETER, RK ;

DEO, N ;

LAGU, B ;

DIETER, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1663-1671

[18]

*ENR NON, 1995, CAD 4 EXPRESS VERS 5

[19]

Farrugia L. J., 1999, Journal of Applied Crystallography, V32, P837, DOI [DOI 10.1107/S0021889812029111, 10.1107/S0021889899006020, DOI 10.1107/S0021889899006020]

[20] Chlorination reactions of ephedrines revisited.: Stereochemistry and functional groups effect on the reaction mechanisms [J].

Flores-Parra, A ;

Suárez-Moreno, P ;

Sánchez-Ruíz, SA ;

Tlahuextl, M ;

Jaen-Gaspar, J ;

Tlahuext, H ;

Salas-Coronado, R ;

Cruz, A ;

Nöth, H ;

Contreras, R .

TETRAHEDRON-ASYMMETRY, 1998, 9 (10) :1661-1671

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