Tetrahedron

Exploring the Stereoselectivity in the Peterson Reaction of Several 2-Substituted 1-Azabicyclo [2.2. 2] octan-3-ones

JE Tønder, M Begtrup, JB Hansen, PH Olesen

文献索引：Tonder, Janne E.; Begtrup, Mikael; Bondo Hansen, John; Olesen, Preben H. Tetrahedron, 2000 , vol. 56, # 8 p. 1139 - 1146

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被引用次数: 6

摘要

The Peterson reaction between a series of 2-substituted 1-azabicyclo [2.2. 2] octan-3-ones and 3-methyl-5-trimethylsilanylmethyl isoxazole (1) was explored.(Z)-Stereoselectivity was obtained with all 2-substituents, ranging from 65: 35 for benzyl to 95: 5 for phenylsulphanyl. Different bases were investigated, revealing that an organolithium base is necessary for the reaction to occur. A transition state is suggested, involving a four-membered ring in which ...