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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

    References

  • 1a Berks AH. Tetrahedron  1996,  52:  331 
    Google Scholar
  • 1b Afonso A. Hon F. Weinstein J. Ganguly AK. McPhail AT.
    J. Am. Chem. Soc.  1982,  104:  6138 
    Google Scholar
  • 1c McCombie SW. Ganguly AK. Med. Res. Rev.  1988,  8:  393 
    Google Scholar
  • 1d Alpegiani M. Bedeschi A. Giudici F. Perrone E. Visentin G. Zarini F. Franceschi G. Heterocycles  1990,  30:  799 
    Google Scholar
  • 1e Corraz AJ. Dax SL. Dunlap NK. Georgopapadakou NH. Keith DD. Pruess DL. Rossman PL. Then R. Unowsky J. Wei CC. J. Med. Chem.  1992,  35:  1828 
    Google Scholar
  • 1f Kondo K. Seki M. Kuroda T. Yamanaka T. Iwasaki T. J. Org. Chem.  1995,  60:  1096 
    Google Scholar
  • 2 Palomo C. Cossio FP. Arrieta A. Odriozola JM. Oiarbide M. Ontoria JM. J. Org. Chem.  1989,  54:  5736 
    CrossrefGoogle Scholar
  • 3 Ito Y. Kawabata T. Terashima S. Tetrahedron Lett.  1986,  27:  5751 
    CrossrefGoogle Scholar
  • 4 Sasaki A. Goda K. Enomoto M. Sunagawa M. Chem. Pharm. Bull.  1992,  40:  1094 
    CrossrefGoogle Scholar
  • 5a Yoshioka T, Watanabe M, Fukagawa Y, and Ishikura T. inventors; WO  8804656. 
  • 5b Goo YM. Lee JH. Cho JS. Lee YY. Bull. Korean Chem. Soc.  1996,  17:  985 
    Google Scholar
  • 6a Hu J. Wu T. Li HG. Xie RG. Gan Y. Lu D. Acta Chim. Sin. (Engl. Ed.)  2001,  59:  279 
    Google Scholar
  • 6b Li HG. Wu T. Xie RG. Hu J. Wang JW. Hu XB. Chem. J. Chin. Univ. (Engl. Ed.)  1999,  20:  1554 
    Google Scholar
  • 7a Kawabata T. Kimura Y. Ito Y. Terashima S. Tetrahedron Lett.  1986,  27:  6241 
    Google Scholar
  • 7b Ito Y. Kobayashi Y. Kawabata T. Takase M. Terashima T. Tetrahedron  1989,  45:  5767 
    Google Scholar
  • 8a Sarko CR. Guch IC. DiMare M. J. Org. Chem.  1994,  59:  705 
    Google Scholar
  • 8b Marcantoni E. Alessandrini S. Malavolta M. J. Org. Chem.  1999,  64:  1986 
    Google Scholar
  • 8c Sarko CR. Collibee SE. Knorr AL. DiMare M. J. Org. Chem.  1996,  61:  868 
    Google Scholar
  • 8d Marcantoni E. Cingolani S. J. Org. Chem.  1998,  63:  3624 
    Google Scholar
  • 8e Bartoli G. Bosco M. Bellucci MC. Dalpozzo R. Marcantoni E. Sambri L. Org. Lett.  2000,  2:  45 
    Google Scholar
  • 9 Zhang H. Chen F.-E. Chen M.-Q. Acta Crystallogr., Sect E.: Struct. Rep. Online  2007,  63:  o3099 
    CrossrefGoogle Scholar
  • 10 Ahn C. Correia R. DeShong P. J. Org. Chem.  2002,  67:  1751 
    CrossrefPubMedGoogle Scholar
  • 11 Shi XX. Shen CL. Yao JZ. Nie LD. Quan N. Tetrahedron: Asymmetry  2010,  21:  277 
    CrossrefGoogle Scholar
  • 12a Zhong Y.-L. Shing TKM. J. Org. Chem.  1997,  62:  2622 
    Google Scholar
  • 12b Chen FE. Zhao JF. Xiong FJ. Xie B. Zhang P. Carbohydr. Res.  2007,  342:  2461 
    Google Scholar
  • 13 Ishibashi H. Kameoka C. Iriyama H. Kodama K. Sato T. Ikeda M. J. Org. Chem.  1995,  60:  1276 
    CrossrefGoogle Scholar
  • 14a Laurent M. Belmans M. Kemps L. Cérésiat M. Marchand-Brynaert J. Synthesis  2003,  570 
    Google Scholar
  • 14b Laurent M. Cérésiat M. Marchand-Brynaert J. J. Org. Chem.  2004,  69:  3194 
    Google Scholar
  • 14c Laurent M. Cérésiat M. Marchand-Brynaert J. Eur. J. Org. Chem.  2006,  3755 
    Google Scholar
  • 15 Wei CC. De Bernardo S. Tengi JP. Borgese J. Weigele M. J. Org. Chem.  1985,  50:  3462 
    CrossrefGoogle Scholar
  • 16 Ireland RE. Obrecht DM. Helv. Chim. Acta  1986,  69:  1273 
    CrossrefGoogle Scholar
  • 17 Seki M. Furutani T. Miyake T. Yamanaka T. Ohmizu H. Tetrahedron: Asymmetry  1996,  7:  1241 
    CrossrefGoogle Scholar