Tetrahedron Letters p. 3289 - 3292 (1999)
Update date:2022-08-17
Topics:
Hu, Yonghang
Porco Jr., John A.
Polystyrene-diethylsilane resin (PS-DES) was treated with triflic acid to form a highly reactive polymer silyl triflate. The silyl triflate reacted with enolizable allylic esters in the presence of Et,N to afford resin-bound silyl ketene acetals, which undergo Ireland-Claisen rearrangement at elevated temperature to provide polymer silyl esters. Transesterification of the polymeric silyl esters with 5% H2SO4 in 1:1 MeOH/ClCH2CH2Cl (DCE) afforded methyl ester products.
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