Tailoring Pt(II) Chiral Catalyst Design for Asymmetric Baeyer-Villiger ­Oxidation of Cyclic Ketones with Hydrogen Peroxide

 

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Abstract

Asymmetric Baeyer-Villiger oxidation of cyclic ketones with hydrogen peroxide mediated by a series of new chiral Pt(II) complexes afforded lactone products in good yields and moderate enantioselectivities.

References

• 1a Strukul G. Angew. Chem. Int. Ed.  1998,  37:  1198 
  CrossrefGoogle Scholar
• 1b ten Grink G.-J. Arends IWCE. Sheldon RA. Chem. Rev.  2004,  104:  4105 
  CrossrefGoogle Scholar
• 1c Renz M. Meunier B. Eur. J. Org. Chem.  1999,  737 
  CrossrefGoogle Scholar
• 2a Noyori R. Aoki M. Sato K. Chem. Commun.  2003,  1977 
  CrossrefGoogle Scholar
• 2b Trost BM. Angew. Chem., Int. Ed. Engl.  1995,  34:  259 
  CrossrefGoogle Scholar
• 3 Gusso A. Baccin C. Pinna F. Strukul G. Organometallics  1994,  13:  3442 
  CrossrefGoogle Scholar
• 4 Bolm C. Schlingloff G. Weickhardt K. Angew. Chem., Int. Ed. Engl.  1994,  33:  1848 
  CrossrefGoogle Scholar
• 5a Bolm C. Luong KK. Schlingloff G. Synlett  1997,  1151 
  CrossrefGoogle Scholar
• 5b Bolm C. Beckmann O. Cosp A. Palazzi C. Synlett  2001,  1461 
  CrossrefGoogle Scholar
• 5c Bolm C. Beckmann O. Palazzi C. Can. J. Chem.  2001,  79:  1593 
  CrossrefGoogle Scholar
• 5d Bolm C. Beckmann O. Kühn T. Palazzi C. Adam W. Bheema Rao P. Saha-Möller CR. Tetrahedron: Asymmetry  2001,  12:  2441 
  CrossrefGoogle Scholar
• 5e Ito K. Ishii A. Kuroda T. Katsuki T. Synlett  2003,  643 
  CrossrefGoogle Scholar
• 5f Watanabe A. Uchida T. Ito K. Katsuki T. Tetrahedron Lett.  2002,  43:  4481 
  CrossrefGoogle Scholar
• 5g Matsumoto K. Watanabe A. Uchida T. Ogi K. Katsuki T. Tetrahedron Lett.  2004,  45:  2385 
  CrossrefGoogle Scholar
• 5h Frison J.-C. Palazzi C. Bolm C. Tetrahedron  2006,  62:  6700 
  CrossrefGoogle Scholar
• 5i Bolm C. Frison J.-C. Zhang Y. Wulff WD. Synlett  2004,  1619 
  CrossrefGoogle Scholar
• 5j Watanabe A. Uchida T. Irie R. Katsuki T. Proc. Natl. Acad. Sci. U.S.A.  2004,  101:  5737 
  CrossrefGoogle Scholar
• 5k Frison J.-C. Palazzi C. Bolm C. Tetrahedron  2006,  62:  6700 
  CrossrefGoogle Scholar
• 6 Paneghetti C. Gavagnin R. Pinna F. Strukul G. Organometallics  1999,  18:  5057 
  CrossrefGoogle Scholar
• 7a Colonna S. Gaggero N. Pasta P. Ottolina G. Chem. Commun.  1996,  2303 
  CrossrefGoogle Scholar
• 7b Roberts SM. Wan PWH. J. Mol. Catal. B: Enzym.  1998,  4:  111 
  CrossrefGoogle Scholar
• 7c Stewart JD. Reed KW. Martinez CA. Zhu J. Chen G. Kayser MM. J. Am. Chem. Soc.  1998,  120:  3541 
  CrossrefGoogle Scholar
• 7d Ottolina G. Bianchi S. Belloni B. Carrea G. Danieli B. Tetrahedron Lett.  1999,  40:  8483 
  CrossrefGoogle Scholar
• 7e Mihovilovic MD. Chen G. Wang S. Kyte B. Rochon F. Kayser MM. Stewart JD. J. Org. Chem.  2001,  66:  733 
  CrossrefGoogle Scholar
• 7f Mihovilovic MD. Müller B. Stanetty P. Eur. J. Org. Chem.  2002,  22:  3711 
  CrossrefGoogle Scholar
• 7g Kamerbeek NM. Janssen DB. van Berkel WJH. Fraaije MW. Adv. Synth. Catal.  2003,  345:  667 
  CrossrefGoogle Scholar
• 7h Ottolina G. de Ponzalo G. Carrea G. Danieli B. Adv. Synth. Catal.  2005,  347:  1035 
  CrossrefGoogle Scholar
• 7i Mihovilovic MD. Chen G. Wang S. Kyte B. Rochon F. Kayser MM. Stewart JD. J. Org. Chem.  2001,  66:  733 
  CrossrefGoogle Scholar
• 8a Kagan HB. Fiaud JC. Top. Stereochem.  1988,  18:  249 
  CrossrefGoogle Scholar
• 8b Keith JM. Larrow JF. Jacobsen EN. Adv. Synth. Catal.  2001,  343:  5 
  CrossrefGoogle Scholar
• 9 Kagan HB. Synlett  2001,  888 
  Article in Thieme ConnectGoogle Scholar
• 10 Gavagnin R. Cataldo M. Pinna F. Strukul G. Organometallics  1998,  17:  661 
  CrossrefGoogle Scholar
• 11 Thuring JWJF. Nefkens GHL. Zwanenburg B. J. Agric. Food Chem.  1997,  45:  2278 
  CrossrefGoogle Scholar
• 12 Clark HC. Manzer LEM. J. Organomet. Chem.  1973,  59:  411 
  Google Scholar