Synthesis of 3-(3S-t-Butoxyl)succinimidyl-β-lactams and the Stereoselectivity of the Reaction

Abstract

Abstract: S-Malic acid is the chiral induction agent widely used in organic synthesis. In order to investigate the stereoselective synthesis of β-lactams, eight new 3-(3S-t-butoxyl)succinimidyl-β-lactam derivatives 2a—2h were obtained by Staudinger reaction using S-malic acid as the chiral induction agent and their structures were confirmed by ¹H NMR, IR and elemental analysis. The stereochemistry of the reaction was also investigated by the ¹H NMR, 2D NMR and X-ray diffraction analyses methods. The results indicate that the reaction of 3-(3S-t-butoxyl)succinimidyl acetyl chloride with imines(under Et₃N) showing very good cis/trans stereoselectivity, and the trans-β-lactam is the only product. The diastereomeric selectivity is also good, the d.e. is between 28%—70%.

Key words: β-Lactam, Schiff base, cis/trans stereoselectivity, Diastereomeric selectivity, Stereoselectivity

CLC Number:

O621

TrendMD:

ZHANG Ping, LIU Na, WANG Lan-Zhi, LI Yuan^*. Synthesis of 3-(3S-t-Butoxyl)succinimidyl-β-lactams and the Stereoselectivity of the Reaction[J]. Chem. J. Chinese Universities, doi: .

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Synthesis of 3-(3S-t-Butoxyl)succinimidyl-β-lactams and the Stereoselectivity of the Reaction

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