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Ester enolate Claisen rearrangement using a polymer-supported silyl triflate

✍ Scribed by Yonghan Hu; John A. Porco Jr.

Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 245 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00441-4

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✦ Synopsis

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 Et3N 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/CICH2CH2CI (DCE) afforded methyl ester products.

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