A stereochemical study of optically active thiazolidines

被引:14
作者
Cruz, A
Vásquez-Badillo, A
Ramos-García, I
Contreras, R
机构
[1] IPN, Ctr Invest & Estudios Avanzados, Dept Quim, Mexico City 07000, DF, Mexico
[2] IPN, Unidad Profes Interdisciplinaria Biotecnol, Dept Quim, Mexico City 07738, DF, Mexico
关键词
D O I
10.1016/S0957-4166(01)00117-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
We report a stereochemical study of a series of free N-H and N-methylated 1,3-thiazolidines heating H or CH, at C-(2). These compounds were readily prepared from ephedrine and pseudoephedrines. The stereochemistry of the compounds under study was deduced using H-1 and C-13 NMR spectroscopy. Two isomers were found for compounds having a methyl group at C-(2) (i.e. C-(2)HCH3): interconversion of these isomers, presumably via a non-cyclic zwitterionic intermediate, was observed. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:711 / 717
页数:7
相关论文
共 18 条
[1]   Asymmetric synthesis and Lewis acid mediated type II carbonyl ene cyclisations of (R)-2-isopropyl-5-methylhex-5-enal [J].
Braddock, DC ;
Brown, JM .
TETRAHEDRON-ASYMMETRY, 2000, 11 (17) :3591-3607
[2]   SuperQuat, (S)-4-benzyl-5,5-dimethyl-oxazolidin-2-one for the asymmetric synthesis of α-substituted aldehydes [J].
Bull, SD ;
Davies, SG ;
Nicholson, RL ;
Sanganee, HJ ;
Smith, AD .
TETRAHEDRON-ASYMMETRY, 2000, 11 (17) :3475-3479
[3]   Diastereoselective photosensitised radical addition to fumaric acid derivatives bearing oxazolidine chiral auxiliaries [J].
Campari, G ;
Fagnoni, M ;
Mella, M ;
Albini, A .
TETRAHEDRON-ASYMMETRY, 2000, 11 (09) :1891-1906
[4]   N-BORANE ADDUCTS OF OXAZOLIDINES DERIVED FROM EPHEDRINE AND PSEUDOEPHEDRINE - STUDY OF STEREOCHEMISTRY BY NUCLEAR MAGNETIC-RESONANCE [J].
CONTRERAS, R ;
SANTIESTEBAN, F ;
PAZSANDOVAL, MA ;
WRACKMEYER, B .
TETRAHEDRON, 1984, 40 (19) :3829-3838
[5]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P1987, DOI 10.1002/(SICI)1521-3773(19980817)37:15<1986::AID-ANIE1986>3.0.CO
[6]  
2-Z
[7]   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
[8]   THIAZABOROLIDINES AND BH3 ADDUCTS DERIVED FROM THIOEPHEDRINES [J].
CRUZ, A ;
FLORESPARRA, A ;
TLAHUEXT, H ;
CONTRERAS, R .
TETRAHEDRON-ASYMMETRY, 1995, 6 (08) :1933-1940
[9]   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
[10]   1-magnesiotetrahydroisoquinolyloxazolines as chiral nucleophiles in stereoselective additions to aldehydes: Auxiliary optimization, asymmetric synthesis of (+)-corlumine, (+)-bicuculline, (+)-egenine, and (+)-corytensine, and preliminary C-13 NMR studies of 1-lithio- and 1-magnesiotetrahydroisoquinolyloxazolines [J].
Gawley, RE ;
Zhang, PS .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8103-8112