- Diastereoface-discrimination reaction of lithium or titanium ester enolates with a chiral imine leading to stereodivergent synthesis of β-lactams
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Diastereoselective addition reaction of ester enolates to a chiral imine possessing (4S, 5S)-4,5-dimethoxymethyl-2-methyl-1,3-dioxolane ring as a chiral auxiliary is reported, in which varying metal enolates resulted in the selective formation of (4S)- or
- Fujisawa, Tamotsu,Ukaji, Yutaka,Noro, Tomohiro,Date, Kengo,Shimizu, Makoto
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p. 5629 - 5638
(2007/10/02)
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- A stereodivergent construction of β-lactam skeletons via condensation of ester enolates and a chiral imine
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Diastereofacial 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.
- Fujisawa, Tamotsu,Ukaji, Yutaka,Noro, Tomohiro,Date, Kengo,Shimizu, Makoto
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p. 7563 - 7566
(2007/10/02)
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