Tetrahedron Letters p. 4281 - 4282 (1996)
Update date:2022-08-17
Topics:
Harrowven, David C.
Poon, Hon Suen
When a solution of diethyl maleate and acetophenone is added to a cooled (-78°C) solution of a lithium amide the maleate derivative 3 is given in good yield. Pre-treatment of the lithium amide with TMSCl alters the course of this reaction dramatically. With half an equivalent of this additive the Michael adduct 4 is given in 62% yield while employing three equivalents leads to the silyl enol ether 5 in >85% yield.
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