Opening of oxabicyclo[3.2.1]octenes with ...
|Title||Opening of oxabicyclo[3.2.1]octenes with organolithium reagents. A route to cyclic and acyclic compounds with high stereocontrol.|
|Author(s)||M. Lautens, A. Abd-El-Aziz, A. Lough|
|Journal||Section Title: Alicyclic Compounds, Journal of Organic Chemistry|
|Abstract||Ring cleavage of oxabicyclo[3.2.1]octenes, e.g., I (R = H, R1 = H, Me, CMe3; R = SiMe2CMe3, R1 = H) occurs in Et2O contg. R3Li (R2 = Me, Bu, Me3C) to give highly substituted cycloheptenes, e.g., II. Silylating the secondary OH group of II (R = H, R1 = Me, R2 = Bu) with Me3CSiMe2Cl in DMF contg. imidazole gave the silyl ether, which underwent oxidative cleavage with O3 followed by redn. of the ozonide with NaBH4 to give the stereocontrolled acyclic tetrol monosilyl ether III, contg. multiple stereocenters. [on SciFinder(R)]|
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