REDUCTIVE RING-OPENING OF EPHEDRINE AND PSEUDOEPHEDRINE-DERIVED OXAZOLIDINIUM METHIODIDES BY SODIUM-BOROHYDRIDE - A DIRECT ACCESS TO NEW CHIRAL AMINE-BORANE ADDUCTS

被引:11
作者
ANDRES, C [1 ]
DELGADO, M [1 ]
PEDROSA, R [1 ]
机构
[1] UNIV VALLADOLID,FAC CIENCIAS,DEPT QUIM ORGAN,DR MERGELINA S-N,E-47011 VALLADOLID,SPAIN
关键词
D O I
10.1080/00397919208020847
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sodiun borohydride reacts with oxazolidinium methiodides derived from ephedrine and pseudoephedrine, in ethereal solvents, cleaving regioselectively the C-N bond of the ring and leading, in good yields, to chiral amine-borane adducts of know absolute configuration. The 1HNMR data allow to predict the most stable conformation.
引用
收藏
页码:829 / 839
页数:11
相关论文
共 25 条
[1]   STEREOCHEMISTRY .60. KINETIC CONTROL OF ASYMMETRIC INDUCTION DURING OXAZOLIDINE FORMATION FROM (-)-EPHEDRINE AND AROMATIC-ALDEHYDES [J].
AGAMI, C ;
RIZK, T .
TETRAHEDRON, 1985, 41 (03) :537-540
[2]  
ALBEROLA A, 1990, HETEROCYCLES, V31, P2079
[3]  
ALBEROLA A, 1990, SYNTHESIS-STUTTGART, P153
[4]  
BHASKAR JV, 1990, J CHEM SOC CHEM COMM, P1145
[5]   ANOMERIC EFFECT - CONFORMATIONAL EQUILIBRIA OF TETRAHYDRO-1,3-OXAZINES AND 1-METHYL-1,3-DIAZANE [J].
BOOTH, H ;
LEMIEUX, RU .
CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (05) :777-&
[6]  
BROWN P, 1983, REPRESENTATIONS, V2, P1
[7]   ASYMMETRIC REDUCTION OF N-SUBSTITUTED KETIMINES WITH THE REAGENT PREPARED FROM BORANE AND (S)-(-)-2-AMINO-3-METHYL-1,1-DIPHENYLBUTAN-1-OL (ITSUNOS REAGENT) - ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE SECONDARY-AMINES [J].
CHO, BT ;
CHUN, YS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3200-3201
[8]   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
[9]   HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553
[10]  
GRUDON MF, 1981, J CHEM SOC P1, P231