Efficient Asymmetric Synthesis of (2R,3R)-3-{(1R)-1-[tert-Butyl(dimethyl)-siloxy]ethyl}-4-oxoazetidin-2-yl Acetate

被引：7

作者：

Huang, Jian-Ping ^{[1
]}

Zhao, Lei ^{[1
]}

Gu, Shuang-Xi ^{[1
]}

Wang, Zhong-Hua ^{[1
]}

Zhang, Hao ^{[1
]}

Chen, Fen-Er ^{[1
,2
]}

Dai, Hui-Fang ^{[3
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

[2] Fudan Univ, Inst Biomed Sci, Shanghai 200032, Peoples R China

[3] Fudan Univ, Sch Pharm, Shanghai 201203, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2011年 / 04期

关键词：

carbapenems; penem; heterocycles; cycloadditions; cyclizations; KEY INTERMEDIATE; BETA-LACTAMS; DIASTEREOSELECTIVE SYNTHESIS; CARBAPENEM SYNTHESIS; (S)-ETHYL LACTATE; PENEM ANTIBIOTICS; HYDROXY KETONES; REDUCTION; (3R; 4R)-4-ACETOXY-3-<(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL>-2-AZETIDINONE; 3-ACETYL-2-AZETIDINONES;

D O I：

10.1055/s-0030-1258407

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(2R,3R)-3-{(1R)-1-[tert-Butyl(dimethyl)siloxy]ethyl}4-oxoazetidin-2-yl acetate was efficiently prepared from L-ascorbic acid. The key steps were the a highly diastereoselective [2 + 2] cycloaddition of diketene with an (S)-glyceraldehyde-derived aldimine to give the ketone, stereoselective titanium tetrachloride mediated asymmetric reduction to give the corrsponding S-configured alcohol, and Mitsunobu inversion of the latter to give the desired R-configured alcohol.

引用

页码：555 / 562

页数：8

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