Tetrahedron Letters p. 5227 - 5230 (1995)
Update date:2022-08-02
Topics: Steric Effects Electronic effects Temperature Control Solvent Choice Chelation Control
Shimizu, Makoto
Kume, Kouji
Fujisawa, Tamotsu
Switchover of the diastereoselectivity was recognized by a simple selection of titanium(IV) halides in the reaction of silyl ketene acetal with a chiral imine possessing a derivative of D-(-)-phenylglycine as an auxiliary. TiF4 effected the formation of (3S)-β-amino ester, while TiCl4 gave (3R)-isomer. The β-amino esters thus obtained were convened into the corresponding β-lactams on treatment with Me3Al without loss of the stereochemical integrity.
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