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Synthesis 2011(4): 555-562  
DOI: 10.1055/s-0030-1258407
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Jian-Ping Huanga, Lei Zhaoa, Shuang-Xi Gua, Zhong-Hua Wanga, Hao Zhanga, Fen-Er Chen*a,b, Hui-Fang Dai*c
a Department of Chemistry, Fudan University, 220 Handan Road, 200433 Shanghai, P. R. of China
b Institute of Biomedical Science, Fudan University, 305 Fenglin Road, 200032 Shanghai, P. R. of China
c School of Pharmacy, Fudan University, 826 Zhangheng Road, 201203 Shanghai, P. R. of China
Fax: +86(21)65643811; e-Mail: rfchen@fudan.edu.cn;
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Publication History

Received 9 November 2010
Publication Date:
17 January 2011 (online)

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Abstract

(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.

Key words

carbapenems - penem - heterocycles - cycloadditions - cyclizations