β-Lithiated enamines as enolate equivalents in Michael additions to enoates. A novel entry to mono- and disubstituted 5-oxo esters
Mono-, di- and trisubstituted tert-butyl 5-amino-4-alkenoates 3 and mono- or disubstituted tert-butyl 5-oxoalkanoates 4 are prepared in good overall yield by conjugate addition of β-lithiated enamines to enoates, followed by quenching with water or iodomethane. In all cases, only one stereoisomer of the polysubstituted enamino esters 3 is produced (de > 98%).
Duhamel,Duhamel,Enders,Karl,Leger,Poirier,Raabe
p. 649 - 654
(2007/10/02)
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