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
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
收藏
页码:909 / 913
页数:5
相关论文
共 49 条
[1]   1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis [J].
Ager, DJ ;
Prakash, I ;
Schaad, DR .
CHEMICAL REVIEWS, 1996, 96 (02) :835-875
[2]   N,2-DILITHIOALKYLAMINES FROM AZIRIDINES BY NAPHTHALENE-CATALYZED REDUCTIVE OPENING - SYNTHETIC APPLICATIONS [J].
ALMENA, J ;
FOUBELO, F ;
YUS, M .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3210-3215
[3]   Total synthesis of (+)-geldanamycin and (-)-o-quinogeldanamycin with use of asymmetric anti- and syn-glycolate aldol reactions [J].
Andrus, MB ;
Meredith, EL ;
Simmons, BL ;
Sekhar, BBVS ;
Hicken, EJ .
ORGANIC LETTERS, 2002, 4 (20) :3549-3552
[4]   Stereoselective 1,4-addition of Grignard reagents to α,β-enamides using a combined chiral auxiliary-catalyst approach [J].
Biswas, Kallolmay ;
Woodward, Simon .
TETRAHEDRON-ASYMMETRY, 2008, 19 (14) :1702-1708
[5]   Chiral bis(amino alcohol)oxalamides as ligands for asymmetric catalysis.: Ti(IV) catalyzed enantioselective addition of diethylzinc to aldehydes [J].
Blay, G ;
Fernández, I ;
Marco-Alelxandre, A ;
Pedro, JR .
TETRAHEDRON-ASYMMETRY, 2005, 16 (06) :1207-1213
[6]   SYNTHESIS OF ARYLAZIRIDINES [J].
BROIS, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (10) :3532-&
[7]  
BROIS SJ, 1966, TETRAHEDRON LETT, P5113
[8]   Tethered Ru(II) catalysts for asymmetric transfer hydrogenation of ketones [J].
Cheung, FK ;
Hayes, AM ;
Hannedouche, J ;
Yim, ASY ;
Wills, M .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) :3188-3197
[9]   A stereochemical study of optically active thiazolidines [J].
Cruz, A ;
Vásquez-Badillo, A ;
Ramos-García, I ;
Contreras, R .
TETRAHEDRON-ASYMMETRY, 2001, 12 (05) :711-717
[10]   Syntheses of optically active 2-(2-benzothiazolylimino)-heterazolidines [J].
Cruz, A ;
Gayosso, M ;
Contreras, R .
HETEROATOM CHEMISTRY, 2001, 12 (07) :586-593