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

来源：

TETRAHEDRON | 1991年 / 47卷 / 08期

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

页码：1435 / 1446

页数：12

共 44 条

[1] COMPOSITION OF MIXED HYDRIDE REAGENTS . A STUDY OF SCHLESINGER REACTION
ASHBY, EC
PRATHER, J
[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
BLANDY, C
GERVAIS, D
CARDENAS, MS
[J]. JOURNAL OF MOLECULAR CATALYSIS, 1986, 34 (01): : 39 - 46
[4] SYNTHESIS OF O-PROTECTED AZIDOHYDRINS CATALYZED BY TITANIUM AND VANADIUM COMPLEXES
BLANDY, C
CHOUKROUN, R
GERVAIS, D
[J]. TETRAHEDRON LETTERS, 1983, 24 (39) : 4189 - 4192
[5] ACID-CATALYZED REACTIONS OF ALIPHATIC AZIDES
BOYER, JH
CANTER, FC
HAMER, J
PUTNEY, RK
[J]. 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
CAMPBELL, MM
CRAIG, RC
REDPATH, J
SAVAGE, DS
SLEIGH, T
[J]. 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
CARON, M
CARLIER, PR
SHARPLESS, KB
[J]. 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
CARON, M
SHARPLESS, KB
[J]. 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
COXON, JM
HARTSHOR.MP
SWALLOW, WH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (08) : 1142 - 1148

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