Synthesis of N-Benzyl-3(S)-phthalimido-4(S)-[4(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-azetidine

Chem. J. Chinese Universities ›› 1999, Vol. 20 ›› Issue (10): 1554.

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Synthesis of N-Benzyl-3(S)-phthalimido-4(S)-[4(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-azetidine

LI Heng-Guang^1,2, WU Tong², XIE Ru-Gang¹, HU Jian¹, WANG Jian-Wei^1,2, HU Xiao-Bin³

1. Department of Chemistry, Sichuan University, Chengdu 610064, China;
2. Sichuan IndustriaLINstitute of Antibiotics, Chengdu 610051, China;
3. Pharmacy School of West China University of Medicine Sciences, Chengdu 610041, China

Received:1998-10-12 Online:1999-10-24 Published:1999-10-24

Abstract

Abstract: (S)-Glyceraldehyde acetonide 4 which is a very useful chiraLINtermidiate in stere-oselective synthesis was prepared conveniently by a new three-step synthetic method from natural chiral resource of L-ascorbic acid 1. The chiral aldehyde condensed with benzyl amine to produce adapted chiraLImine 5. The imine is unstable, but it can carry a [2+2] cyclic addition with ketene 8 which was obtained from phthalimidoacetyl chloride and triethylamine under mild conditions, and produce the title compound, N-benzyl-3-(S)-phthalimido-4-(S)-[4(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-azetidine. Because of the high facial stereoselection in cyclic addition mechanism and attacking with ketene in unblocked face of the imine, the optical purity of the final product is quite satisfactory.

Key words: β-Lactam, L-Ascorbic acid, ChiraLImine, Ketene, [2+2] Cyclic addition

CLC Number:

O624.6

TrendMD:

LI Heng-Guang, WU Tong, XIE Ru-Gang, HU Jian, WANG Jian-Wei, HU Xiao-Bin . Synthesis of N-Benzyl-3(S)-phthalimido-4(S)-[4(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-azetidine[J]. Chem. J. Chinese Universities, 1999, 20(10): 1554.

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Synthesis of N-Benzyl-3(S)-phthalimido-4(S)-[4(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxo-azetidine

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