Tetrahedron: Asymmetry

Synthesis and ene reactions of di-(−)-menthyl diazenedicarboxylate

MA Brimble, CH Heathcock, GN Nobin

Index: Brimble, Margaret A.; Heathcock, Clayton H.; Nobin, Gregory N. Tetrahedron Asymmetry, 1996 , vol. 7, # 7 p. 2007 - 2016

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Citation Number: 25

Abstract

The preparation di-(−)-menthyl diazendicarboxylate 3 is described. Reaction of hydrazine with excess (−)-menthyl chloroformate 1 afforded dimenthyl diazanedicarboxylate 2 which was then oxidized to the azo-enophile 3. The azo-ene reactions of 3 with the alkenes trans-3- hexene 4, trans-4-octene 6, cyclohexene 8 and cyclopentene 10 were carried out using the Lewis acid catalyst tin tetrachloride. Trans-3-hexene 4 and trans-4-octene 6 afforded the ...