Tetrahedron

Highly regio and chemoselective ring opening of epoxides with trimethylsilyl azide in the presence of aluminium isopropoxide and titanium isopropoxide

KI Sutowardoyo, M Emziane, P Lhoste, D Sinou

Index: Sutowardoyo, Kun I.; Emziane, Mohamed; Lhoste, Paul; Sinou, Denis Tetrahedron, 1991 , vol. 47, # 8 p. 1435 - 1446

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Citation Number: 48

Abstract

The ring-opening of functionalized epoxides with trimethylsilyl azide in the presence of a catalytic amount of Ti (Oi-Pr) 4 or Al (Oi-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.