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Synthesis 2009(11): 1881-1885  
DOI: 10.1055/s-0028-1088047
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Reduction of Prochiral Ketones Employing Sprouted Pisum sativa as Biocatalyst

Jhillu S. Yadav*, Basi V. Subba Reddy, Chittamuru Sreelakshmi, Adari Bhaskar Rao
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
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Publication History

Received 19 January 2009
Publication Date:
14 April 2009 (online)

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Abstract

Sprouted green peas have been used for the first time as biocatalysts for enantioselective reduction of prochiral ketones. The reactions are highly enantioselective to furnish chiral alcohols in good yields. The sprouted peas as biocatalysts are a cheap and easy way for generating some interesting chiral alcohols. This process is efficient and convenient to produce chiral secondary alcohols in water.

Key words

biocatalysis - ketones - enantioselective - chiral alcohols

    References

  • 1a Alfermann A. Biocatalysis in Organic Synthesis   Tramper J. van der Plas H. Linko P. Elsevier; Amsterdam: 1985.  p.25 
  • 1b Plant Cell Culture: A Practical Approach   Dixon RA. IRL Press; Eynsham: 1985. 
  • 2a Jones JB. In Comprehensive Organic Synthesis   Vol. 8:  Fleming I. Trost B. M. Pergamon Press; Oxford: 1991.  p.183 
    Search in Google Scholar
  • 2b Ward OP. Young CS. Enzyme Microbiol. Technol.  1998,  12:  482 
    Search in Google Scholar
  • 2c Nayori R. Asymmetric Catalysis in Organic Synthesis   Wiley; New York: 1994. 
  • 3 Ishihara K. Hamada H. Hirata T. Nakajima N. J. Mol. Catal. B: Enzym.  2003,  23:  145 
    CrossrefSearch in Google Scholar
  • 4 Cordell GA. Lemos TLG. Monte FJQ. de Mattos MC. J. Nat. Prod.  2007,  70:  478 
    CrossrefSearch in Google Scholar
  • 5 Blanchard N. Weghe PVD. Org. Biomol. Chem.  2006,  4:  2348 
    CrossrefSearch in Google Scholar
  • 6a Akakabe Y. Takahashi M. Kamezawa M. Kikuchi K. Tachibana H. Ohtani T. Naoshima Y. J. Chem. Soc., Perkin Trans. 1  1995,  1295 
  • 6b Baskar B. Ganesh S. Lokeswari TS. Chadka A. J. Mol. Catal. B: Enzym.  2004,  27:  13 
    Search in Google Scholar
  • 7a Baldassarre F. Bertoni G. Chiappe C. Marioni F. J. Mol. Catal. B: Enzym.  2000,  11:  55 
    Search in Google Scholar
  • 7b Yadav JS. Reddy PT. Hashim SR. Synlett  2000,  1049 
  • 7c Yadav JS. Reddy PT. Hashim SR. Synlett  2000,  473 
  • 7d Maczka WK. Mironowicz A. Tetrahedron: Asymmetry  2002,  13:  2299 
    Search in Google Scholar
  • 8a Stampfer W. Kosjek B. Faber K. Kroutil W. J. Org. Chem.  2003,  68:  402 
    Search in Google Scholar
  • 8b Gröger H. Hummel W. Rollmann C. Chamouleau F. Hüsken H. Werner H. Wunderlich C. Abokitse K. Drauz K. Buchholz S. Tetrahedron  2004,  60:  633 
    Search in Google Scholar
  • 8c Edegger K. Stampfer W. Seisser B. Faber K. Mayer SF. Oehrlein R. Hafner A. Kroutil W. Eur. J. Org. Chem.  2006,  1904 
  • 8d Yang Z.-H. Zeng R. Yang G. Wang Y. Li L.-Z. Lv Z.-S. Yao M. Lai B. J. Ind. Microbiol. Biotechnol.  2008,  35:  1047 
    Search in Google Scholar
  • 9a Yadav JS. Nanda S. Reddy PT. Rao AB. J. Org. Chem.  2002,  67:  3900 
    Search in Google Scholar
  • 9b Caron D. Coughlan AP. Simard M. Bernier J. Piche Y. Chenevert R. Biotech. Lett.  2005,  27:  713 
    Search in Google Scholar
  • 9c Scarpi D. Occhiato EG. Guarna A. Tetrahedron: Asymmetry  2005,  16:  1479 
    Search in Google Scholar
  • 9d Mazczka WK. Mironowicz A. Tetrahedron: Asymmetry  2004,  15:  1965 
    Search in Google Scholar
  • 9e Comasseto JV. Omori AT. Porto ALM. Andrade LH. Tetrahedron Lett.  2004,  45:  473 
    Search in Google Scholar
  • 9f Maczka WK. Mironowicz A. Tetrahedron: Asymmetry  2002,  13:  2299 
    Search in Google Scholar
  • 10 Kumaraswamy G. Ramesh S. Green Chem.  2003,  5:  306 
    CrossrefSearch in Google Scholar
  • 11a Haslegrave JA. Jones JB. J. Am. Chem. Soc.  1982,  104:  4667 
    Search in Google Scholar
  • 11b Harada T. Kurokawa H. Kagamihara Y. Tanaka S. Inoue A. Oku A. J. Org. Chem.  1992,  57:  1412 
    Search in Google Scholar
  • 11c Nunez MT. Martin VS. J. Org. Chem.  1990,  55:  1928 
    Search in Google Scholar
  • 11d Yadav JS. Reddy BVS. Padmavani B. Venugopal Ch. Rao AB. Tetrahedron Lett.  2007,  48:  4613 
    Search in Google Scholar
  • 11e Yadav JS. Reddy BVS. Sreelakshmi Ch. Narayana Kumar GGKS. Rao AB. Tetrahedron Lett.  2008,  49:  2768 
    Search in Google Scholar
  • 12 Prelog V. Pure Appl. Chem.  1964,  9:  119 
    CrossrefSearch in Google Scholar