Journal of Organic Chemistry p. 5301 - 5303 (1993)
Update date:2022-08-05
Topics:
Hattori, Kouji
Yamamoto, Hisashi
A method for the stereoselective synthesis of silyl ketene acetals from α-hydroxy esters is described.Internal quench with excess TMSCl of the lithium enolate at -100 deg C, which is generated using a hindered base, LTMP, leads to the selective formation of (E)-silyl ketene acetal.In contrast, the deprotonation t -100 deg C using LHMDS in THF-HMPA (4:1), followed by treatment with tert-butyldimethylsilyl chloride affords the (Z)-silyl ketene acetal selectively.The method can be applied to the stereoselective reaction of the Ireland ester enolate Claisen rearrangement and aldol synthesis.
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Doi:10.1021/op400300t
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(1993)