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Efficient asymmetric Baeyer–Villiger oxidation of prochiral cyclobutanones using new polymer-supported and unsupported chiral co(salen) complexes

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Abstract

Two heterogeneous catalysts 4 and 5 and three homogenous complexes 1–3 were prepared and used for enantioselective Baeyer–Villiger (B–V) oxidation of prochiral cyclobutanones. Among the prepared catalysts, the supported ones showed better enantioselectivity, good thermal stability and negligible loss of activity over consecutive recycling offset by lower chemical yield.

We report here an efficient method for asymmetric Baeyer–Villiger oxidation of prochiral cyclobutanones using new polymer-supported and unsupported chiral co(salen) complexes.

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References

  1. Baeyer V and Villiger B 1899 Dtsch. Chem. Ges. 32 3625

    Article  Google Scholar 

  2. Del Todesco Frisone M, Pinna F and Strukul G 1993 Organometallics 12 148

    Article  Google Scholar 

  3. (a) Strukul G 1998 Angew. Chem. 110 1256; (b) ten Brink G J, Arends I W C E and Sheldon R A 2004 Chem. Rev. 104 4105; (c) Renz M and Meunier B 1999 Eur. J. Org. Chem. 737

  4. Uchida T and Katsuki T 2001 Tetrahedron Lett. 42 6911

    Article  Google Scholar 

  5. Bolm C, Schlingloff G and Weickhardt K 1994 Angew. Chem. 106 1944

    Article  CAS  Google Scholar 

  6. Bolm C, Khanh Luong T K and Schlingloff G 1997 Synlett. 1151

  7. (a) Ito K, Ishii A, Kuroda T and Katsuki T 2003 Synlett. 0643; (b) Malkov A V, Friscourt F, Bell M, Swarbrick M E and Kochovsky P 2008 J. Org. Chem. 73 3996; (c) Uchida T and KatsukiHelvetica T 2002 Chemica. Acta. 85 3078

  8. Paneghetti C, Gavagnin R, Pinna F and Strukul G 1999 Organometallics 18 5057

    Article  CAS  Google Scholar 

  9. (a) Watanabe A, Uchida T, Irie R and Katsuki T 2004 Proc. Natl. Acad. Sci. 101 5737; (b) Bolm C and Beckmann O 2000 Chirality 12 523

  10. Matsumoto K, Watanabe A, Uchida T, Ogi K and Katsuki T 2004 Tetrahedron Lett. 45 2385

    Article  CAS  Google Scholar 

  11. Bolm C, Beckmann O, Cosp A and Palazzi C 2001 Synlett. 1461

  12. (a) Bolm C, Frison J C, Zhang Y and Wulff W D 2004 Synlett. 1619; (b) Frison J C, Palazzi C and Bolm C 2006 Tetrahedron 62 6700; (c) Bolm C, Beckmann O, Palazzi C, Adam W, Bheema Rao P and Saha-Mçller C R 2001 Tetrahedron: Asymmetry 12 2441; (d) Bolm C, Beckmann O and Palazzi C 2001 Can. J. Chem. 79 1593

  13. Kelly D R 2000 Chem. Oggi./Chem. Today 18 33

    CAS  Google Scholar 

  14. (a) Fukuda T and Katsuki T 1995 Synlett. 825; (b) Fukuda T and Katsuki T 1996 Tetrahedron Lett. 37 4389

  15. (a) Tokunaga M, Larrow J F, Kakiuchi F and Jacobsen E N 1997 Science 277 936; (b) Ready J M and Jacobsen E N 1999 J. Am. Chem. Soc. 121 6086

  16. Saito B and Katsuki T 2001 Tetrahedron Lett. 42 3873

    Article  CAS  Google Scholar 

  17. Cheng M C, Chang M C W, Peng S M, Cheung K K and Che C M 1997 J. Chem. Soc. Dalton Trans. 3479

  18. Schmit C, Falmagne J B, Escudero J, Vanlierde H and Ghosez L 1990 Org. Synth. 69 199

    CAS  Google Scholar 

  19. Kelly D R, Knowles C J, Mahdi J G, Wright M A, Taylor I N and et al 1995 J. Chem. Soc. Perkin Trans. 1 2057

    Article  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, University of Birjand, Birjand, Iran

    REZA SANDAROOS

  2. Department of Chemistry, Islamic Azad University, Birjand Branch, Birjand, Iran

    MOHAMMAD TAGHI GOLDANI

  3. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran

    SAMAN DAMAVANDI

  4. Department of Chemistry, Sarvestan Branch, Islamic Azad University, Sarvestan, Iran

    ALI MOHAMMADI

Authors
  1. REZA SANDAROOS
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  2. MOHAMMAD TAGHI GOLDANI
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  3. SAMAN DAMAVANDI
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  4. ALI MOHAMMADI
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Correspondence to REZA SANDAROOS.

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SANDAROOS, R., GOLDANI, M.T., DAMAVANDI, S. et al. Efficient asymmetric Baeyer–Villiger oxidation of prochiral cyclobutanones using new polymer-supported and unsupported chiral co(salen) complexes. J Chem Sci 124, 871–876 (2012). https://doi.org/10.1007/s12039-012-0277-6

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  • DOI: https://doi.org/10.1007/s12039-012-0277-6

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