Asymmetric mannich reactions with α-silylated trimethylsilyl enol ethers and N-alkoxycarbonyl imines
The Mannich reaction of enantiomerically pure α-dimethylthexylsilylated trimethylsilyl enol ether (Z,S)-2 with titanium complexes of N-alkoxycarbonyl imines afforded α′-silylated αβ-disubstituted β-amino ketones (S,R,S)-4a-e in good to excellent yields (70-92percent) and diastereomeric excesses (de ≥ 96percent). Removal of the directing silyl group gave N-protected and anti-configured β-amino ketones (R,S)-5a-e in excellent yields (90-95percent) and stereoselectivities (de, ee ≥ 96percent- > 98percent).
Enders, Dieter,Oberbo?rsch, Stefan
p. 471 - 473
(2007/10/03)
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