THIAZABOROLIDINES AND BH3 ADDUCTS DERIVED FROM THIOEPHEDRINES

被引:22
作者
CRUZ, A
FLORESPARRA, A
TLAHUEXT, H
CONTRERAS, R
机构
[1] INST POLITECN NACL,CTR INVEST & ESTUDIOS AVANZADOS,MEXICO CITY 07000,DF,MEXICO
[2] UNIV AUTONOMA ESTADO MORELOS,FAC CIENCIAS,CUERNAVACA,MORELOS,MEXICO
关键词
D O I
10.1016/0957-4166(95)00252-K
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The synthesis of 1,3,2-thiazaborolidine and 2,3-dihydro-2, 1,3-borathiazolidines from reaction of ephedrine disulfide and 3,4-dimethyl-5-phenyl-1,3-thiazolidine-2-thione with BH3-THF is reported. The two reactions afforded optically active borohydride heterocycles. The X-ray diffraction structure of (1R,2R)-(-)-chlorodeoxy-pselrdo-ephedrine hydrochloride, (1R,2R)-(-)-thiosulfonic deoxy-pseudo-ephedrine and (3S,4R,5R)-(+)-2,3-dihydro-3,4-dimethyl-5-phenyl-2, 1,3-borathiazolidine are reported.
引用
收藏
页码:1933 / 1940
页数:8
相关论文
共 11 条
[1]   POTENTIAL RADIATION PROTECTIVE AGENTS .3. MERCAPTO ANALOGS RELATED TO EPHEDRINE [J].
BHAT, KV ;
MCCARTHY, WC .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1965, 54 (02) :225-&
[2]   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
[3]   STEREOCHEMICAL COURSE OF THE REACTION OF 2-HALOETHYL ISOTHIOCYANATES WITH NUCLEOPHILES - STEREOSPECIFIC ROUTE TO 4,5-DISUBSTITUTED DELTA-2-THIAZOLINES AND THIAZOLIDINE-2-THIONES [J].
KNIEZO, L ;
KRISTIAN, P ;
BUDESINSKY, M ;
HAVRILOVA, K .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1981, 46 (03) :717-728
[4]  
KONE B, 1983, B SOC CHIM BELG, V92, P139
[5]   C-13 NMR-STUDIES OF OXAZOLIDINES, N-BORANE OXAZOLIDINES AND OXAZOLIDINIUM SALTS DERIVED FROM PSEUDOEPHEDRINE - STERIC EFFECT OF THE BH3 AND CH3 GROUPS ON THE CHEMICAL-SHIFTS [J].
PAZSANDOVAL, MA ;
SANTIESTEBAN, F ;
CONTRERAS, R .
MAGNETIC RESONANCE IN CHEMISTRY, 1985, 23 (06) :428-431
[6]   SPIROBORATES DERIVED FROM CATECHOLBORANE AND EPHEDRINE TYPE AMINOALCOHOLS - MODEL COMPOUNDS FOR THE STUDY OF INTRAMOLECULAR N-]B COORDINATION BY DYNAMIC H-1-NMR, B-11-NMR AND C-13-NMR [J].
SANTIESTEBAN, F ;
CAMPOS, MA ;
MORALES, H ;
CONTRERAS, R ;
WRACKMEYER, B .
POLYHEDRON, 1984, 3 (05) :589-594
[7]   DETERMINATION OF THE NITROGEN CONFIGURATION IN EPHEDRINE N-BORANES AND A STUDY OF THEIR ASSISTED STEREOSPECIFIC DEUTERATION OF NH [J].
TLAHUEXT, H ;
SANTIESTEBAN, F ;
GARCIABAEZ, E ;
CONTRERAS, R .
TETRAHEDRON-ASYMMETRY, 1994, 5 (08) :1579-1588
[8]   DIBORANE DERIVATIVES FROM N-ALKYLOXAZABOROLIDINES [J].
TLAHUEXT, H ;
CONTRERAS, R .
TETRAHEDRON-ASYMMETRY, 1992, 3 (09) :1145-1148
[9]   N-ALKYLOXAZABOROLIDINES DERIVED FROM EPHEDRINES [J].
TLAHUEXT, H ;
CONTRERAS, R .
TETRAHEDRON-ASYMMETRY, 1992, 3 (06) :727-730
[10]  
WATKIN DJ, 1988, CRYSTAL ADV CRYSTALL