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

[41] REGIOSELECTIVE OPENING OF EPOXIDE RINGS WITH ME3SIN3 CATALYZED BY TI(O-IPR)4
SINOU, D
EMZIANE, M
[J]. TETRAHEDRON LETTERS, 1986, 27 (37) : 4423 - 4426
[42] TSENG CC, 1977, CHEM PHARM BULL, V52, P1013
[43] THE REACTION OF SODIUM AZIDE WITH SOME REPRESENTATIVE EPOXIDES
VANDERWERF, CA
HEISLER, RY
MCEWEN, WE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (05) : 1231 - 1235
[44] AN IMPROVED SYNTHESIS OF CARBOCYCLIC AND HETEROCYCLIC ARENE IMINES
WEITZBERG, M
AIZENSHTAT, Z
JERUSHALMY, P
BLUM, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (21) : 4252 - 4254

← 1 2 3 4 5 →