Changing course with an additive: A striking example of the effect of TMSCl on lithium amide reactivity
1996; Elsevier BV; Volume: 37; Issue: 24 Linguagem: Inglês
10.1016/0040-4039(96)00817-9
ISSN1873-3581
AutoresDavid C. Harrowven, Hon Suen Poon,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoAbstract 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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