A stereodivergent construction of β-lactam skeletons via condensation of ester enolates and a chiral imine
1991; Elsevier BV; Volume: 32; Issue: 51 Linguagem: Inglês
10.1016/0040-4039(91)80535-e
ISSN1873-3581
AutoresTamotsu Fujisawa, Yutaka Ukaji, Tomohiro Noro, Kengo Date, Makoto Shimizu,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoDiastereofacial selectivity in an addition reaction of ester enolates to a chiral imine with 1,3-dioxolane, derived from (S,S)-1,4-dimethoxy-2,3-butanediol as a chiral auxiliary, could be fully regulated by the appropriate selection of metal enolates used. Addition of the lithium enolates provided (4S)-β-lactams, while the corresponding (4R)-β-lactams were obtained by the condensation of titanium enolates with the chiral imine.
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