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

被引:23
|
作者
Brimble, MA [1 ]
Heathcock, CH [1 ]
Nobin, GN [1 ]
机构
[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720
基金
澳大利亚研究理事会;
关键词
D O I
10.1016/0957-4166(96)00242-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
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 ene adducts 5 (80%) and 7 (70%) with a diastereomeric excess of 2.5:1 and 2:1 respectively. Use of cyclohexene 8 and cyclopentene 10 afforded the ene adducts 9 and 11 in 81% and 88% yield, however, no diastereomeric excess was observed. Finally use of conjugated aromatic acyclic alkenes 12 and 14 afforded the chlorides 13 and 15 in 93% and 56% yield respectively. In these latter cases an ionic addition proceeded rather than a pericyclic ene reaction. Attempted removal of the chiral menthyl ester auxiliary from the ene adduct 5 proved difficult. Copyright (C) 1996 Published by Elsevier Science Ltd
引用
收藏
页码:2007 / 2016
页数:10
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