Applications of the β-azidonation reaction to organic synthesis. α, β-Enones, conjugate addition, and γ-lactam annulation

P Magnus, J Lacour, PA Evans…

Index: Magnus, Philip Journal of the American Chemical Society, 1998 , vol. 120, # 48 p. 12486 - 12499

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Citation Number: 22

Abstract

The β-azido functionalization reaction provides a mechanistically different enone synthesis that involves treatment of 2 with fluoride anion to effect desilylation and concomitant β- elimination to give 3. Table 1 lists a number of examples of the direct conversion of a TIPS enol ether into the corresponding α, β-enone via a β-azido TIPS enol ether. The β-azido group can be ionized with Me3Al or Me2AlCl and the intermediate enonium ion trapped ...