HIGHLY REGIO AND CHEMOSELECTIVE RING-OPENING OF EPOXIDES WITH TRIMETHYLSILYL AZIDE IN THE PRESENCE OF ALUMINUM ISOPROPOXIDE AND TITANIUM ISOPROPOXIDE

被引:50
作者
SUTOWARDOYO, KI [1 ]
EMZIANE, M [1 ]
LHOSTE, P [1 ]
SINOU, D [1 ]
机构
[1] UNIV LYON 1,SYNTHESE ASYMET LAB,CNRS,43 BLVD 11 NOVEMBRE 1918,F-69622 VILLEURBANNE,FRANCE
关键词
D O I
10.1016/S0040-4020(01)86420-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ring-opening of functionalized epoxides with trimethylsilyl azide in the presence of a catalytic amount of Ti(O-i-Pr)4 or Al(O-i-Pr)3 is described. The reaction is stereospecific and highly regiospecific, leading generally to the formation of the carbon-azido bond on the less substituted carbon. The mechanism of this reaction is also discussed.
引用
收藏
页码:1435 / 1446
页数:12
相关论文
共 44 条
[1]   COMPOSITION OF MIXED HYDRIDE REAGENTS . A STUDY OF SCHLESINGER REACTION [J].
ASHBY, EC ;
PRATHER, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (04) :729-&
[2]  
BIRKOFER L, 1975, LIEBIGS ANN CHEM, P266
[3]   THE ROLE OF EARLY TRANSITION-METAL AZIDES AS CATALYSTS OF THE RING-OPENING REACTION OF EPOXIDES WITH TRIMETHYLSILYLAZIDE [J].
BLANDY, C ;
GERVAIS, D ;
CARDENAS, MS .
JOURNAL OF MOLECULAR CATALYSIS, 1986, 34 (01) :39-46
[4]   SYNTHESIS OF O-PROTECTED AZIDOHYDRINS CATALYZED BY TITANIUM AND VANADIUM COMPLEXES [J].
BLANDY, C ;
CHOUKROUN, R ;
GERVAIS, D .
TETRAHEDRON LETTERS, 1983, 24 (39) :4189-4192
[5]   ACID-CATALYZED REACTIONS OF ALIPHATIC AZIDES [J].
BOYER, JH ;
CANTER, FC ;
HAMER, J ;
PUTNEY, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (02) :325-327
[6]   AMINO-STEROIDS .7. SYNTHESIS OF 3ALPHA-AMINO-2BETA-HYDROXY-ANDROST-5-EN-17-ONE AND 2BETA-AMINO-3ALPHA-HYDROXY-ANDROST-5-EN-17-ONE [J].
CAMPBELL, MM ;
CRAIG, RC ;
REDPATH, J ;
SAVAGE, DS ;
SLEIGH, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (12) :3042-3047
[7]   REGIOSELECTIVE AZIDE OPENING OF 2,3-EPOXY ALCOHOLS BY [TI(O-I-PR)2(N3)2] - SYNTHESIS OF ALPHA-AMINO-ACIDS [J].
CARON, M ;
CARLIER, PR ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5185-5187
[8]   TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING [J].
CARON, M ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1557-1560
[9]  
CHAUTEMPS P, 1968, CR ACAD SCI C CHIM, V266, P622
[10]   STUDY OF ACETATE PARTICIPATION IN ACYCLIC EPOXIDE SYSTEMS - ACID-CATALYZED REARRANGEMENTS OF TRANS AND CIS-1-ACETOXY-3,4-EPOXYPENTANES, -4,5-EPOXYHEXANES, AND -5,6-EPOXYHEPTANES [J].
COXON, JM ;
HARTSHOR.MP ;
SWALLOW, WH .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (08) :1142-1148