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Synthesis 2009(15): 2627-2633  
DOI: 10.1055/s-0029-1217405
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Hydrogenation of β-N-Substituted and β-N,N-Disubstituted Enamino Esters in the Presence of Iridium(I) Catalyst

Hania Hebbachea,b, Zakia Hanka, Christian Bruneau*b, Jean-Luc Renaud*c
a Laboratoire d’Électrochimie-Corrosion, Métallurgie et Chimie Minérale, Université des Sciences et Technologies Houari Boumedienne, Faculté de Chimie, BP32 El Alia 16111 Bab-Ezzouar, Alger, Algérie
b UMR 6226, CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Catalyse et Organométalliques, Campus de Beaulieu, 35042 Rennes Cedex, France
Fax: +33(2)23236939; e-Mail: christian.bruneau@univ-rennes1.fr;
c Laboratoire de Chimie Moléculaire et Thioorganique, UMR 6507, INC3M, FR 3038, ENSICAEN-Université de Caen, 14050 Caen, France
Fax: 33(2)31452877; e-Mail: jean-luc.renaud@ensicaen.fr;
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Publikationsverlauf

Received 3 April 2009
Publikationsdatum:
22. Juni 2009 (online)

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Abstract

Several new β-amino esters were prepared in two simple steps from β-keto ester derivatives and primary and secondary amines under mild conditions. The hydrogenation of various enamino esters was performed at 50 ˚C in the presence of iridium catalysts. The new β-N-substituted amino esters were isolated in high yields.

Key words

catalysis - hydrogenation - iridium - β-amino esters

    References

  • 1a Gademann K. Hintermann T. Schreiber JV. Curr. Med. Chem.  1999,  6:  905 
    Google Scholar
  • 1b Gellman SH. Acc. Chem. Res.  1998,  31:  173 
    Google Scholar
  • 1c Hoekstra WJ. Curr. Med. Chem.  1999,  6:  7940 
    Google Scholar
  • 1d Juaristi E. Enantioselective Synthesis of β-Amino Acids   Wiley-VCH; New York: 1997. 
    Google Scholar
  • 1e Guenard D. Guéritte-Voegelein R. Potier P. Acc. Chem. Res.  1993,  26:  160 
    Google Scholar
  • 1f Seebach D. Matthews JL. Chem. Commun.  1997,  2015 
    Google Scholar
  • 2a Konichi M. Nishio M. Saitoh T. Miyaki T. Oki T. Kawaguchi H. J. Antibiot.  1989,  42:  1749 
    Google Scholar
  • 2b Oki T. Hirano M. Tomatsu K. Numata K. Kamei H. J. Antibiot.  1989,  42:  1756 
    Google Scholar
  • 3 Shinagawa S. Kanamaru T. Harada S. Asai M. Okazaki H. J. Med. Chem.  1987,  30:  1458 
    CrossrefPubMedGoogle Scholar
  • 4a Namikoshi M. Rinehart KL. Dahlem AM. Beasley VR. Carmichael WW. Tetrahedron Lett.  1989,  30:  4349 
    Google Scholar
  • 4b Roers R. Verdine GL. Tetrahedron Lett.  2001,  42:  3563 
    Google Scholar
  • 4c Wehner V. Blum H. Kurz M. Stilz HU. Synthesis  2002,  2023 
    Google Scholar
  • 4d Bull SD. Davies SG. Fox DJ. Gianotti M. Kelly PM. Pierres C. Savory ED. Smith AD. J. Chem. Soc., Perkin Trans. 1  2002,  1858 
    Google Scholar
  • 5a Crews P. Manes L. Boehler M. Tetrahedron Lett.  1986,  27:  2797 
    Google Scholar
  • 5b Shih C. Gossett LS. Gruber JM. Grossman CS. Andis SL. Schultz RM. Worzalla JF. Corbett TH. Metz JT. Bioorg. Med. Chem. Lett.  1999,  9:  69 
    Google Scholar
  • 6a Lui M. Sibi MP. Tetrahedron  2002,  58:  7991 
    Google Scholar
  • 6b Abele S. Seebach D. Eur. J. Org. Chem.  2000,  1 
    Google Scholar
  • See for example:
  • 7a Yuan C. Williams RM. J. Am. Chem. Soc.  1997,  119:  11777 
    Google Scholar
  • 7b Yang H. Foster K. Stephenson CRJ. Brown W. Roberts E. Org. Lett.  2000,  2:  2177 
    Google Scholar
  • 8 Gedey S. Liljeblad A. Lázár L. Fülöp F. Kanerva LT. Tetrahedron: Asymmetry  2001,  12:  105 ; and references cited therein
    CrossrefGoogle Scholar
  • See for example:
  • 9a Tang TP. Ellman JA. J. Org. Chem.  2002,  67:  7819 
    Google Scholar
  • 9b Wenzel AG. Jacobsen EN. J. Am. Chem. Soc.  2002,  124:  12964 
    Google Scholar
  • 9c Murahashi S.-i. Imada Y. Kawakami T. Harada K. Yonemushi Y. Tomita N. J. Am. Chem. Soc.  2002,  124:  2888 
    Google Scholar
  • 9d Miaybe H. Fujii K. Goto T. Naito T. Org. Lett.  2000,  2:  4071 
    Google Scholar
  • See for example:
  • 10a Sibi MP. Deshpande PK. J. Chem. Soc., Perkin Trans. 1  2000,  1461 
    Google Scholar
  • 10b Evans DA. Wu LD. Wiener JJM. Johnson JS. Ripin DHB. Tedrow JS. J. Org. Chem.  1999,  64:  6411 
    Google Scholar
  • See for example:
  • 11a Sibi MP. Shay JJ. Liu M. Jasperse CP. J. Am. Chem. Soc.  1998,  120:  6615 
    Google Scholar
  • 11b Sibi MP. Asano Y. J. Am. Chem. Soc.  2001,  123:  9708 
    Google Scholar
  • 11c Doi H. Sakai T. Iguchi M. Yamada K.-i. Tomioka K. J. Am. Chem. Soc.  2003,  125:  2886 
    Google Scholar
  • 11d Myers JK. Jacobsen EN. J. Am. Chem. Soc.  1999,  121:  8959 
    Google Scholar
  • 11e Guerin DJ. Miller SJ. J. Am. Chem. Soc.  2002,  124:  2134 
    Google Scholar
  • See for example:
  • 12a Bruncko M. Schlingoff G. Sharpless KB. Angew. Chem,. Int. Ed. Eng.  1997,  36:  1483 
    Google Scholar
  • 12b O’Brien P. Angew. Chem. Int. Ed.  1999,  38:  326 
    Google Scholar
  • 13a For recent examples, see: For a review, see: Palomo C. Aizpurua JM. Ganboa I. Oiarbide M. Eur. J. Org. Chem.  1999,  3223 
    Google Scholar
  • 13b Hodous BL. Fu GC. J. Am. Chem. Soc.  2002,  124:  1578 
    Google Scholar
  • 13c Lo MM.-C. Fu GC. J. Am. Chem. Soc.  2002,  124:  4572 
    Google Scholar
  • 14 Bruneau C. Renaud J.-L. Jerphagnon T. Coord. Chem. Rev.  2008,  252:  532 
    CrossrefGoogle Scholar
  • 15a Spindler F. Blaser H.-U. In Handbook of Homogeneous Hydrogenation   de Vries JG. Elsevier CJ. Wiley-VCH; Weinheim: 2007.  p.1193-1214  
    Google Scholar
  • 15b Tararov VI. Kadyrov R. Riermeier TH. Holz J. Börner A. Tetrahedron Lett.  2000,  41:  2351 
    Google Scholar
  • 15c Tavarov VI. Börner A. Synlett  2005,  203 
    Google Scholar
  • 16a Hsiao Y. Rivera NR. Rosner T. Krska SW. Njolito E. Wang F. Sun Y. Armstrong JD. Grabowski EJJ. Tillyer RD. Spindler F. Malan C. J. Am. Chem. Soc.  2004,  126:  9918 
    Google Scholar
  • 16b Xiao Y, Armstrong JD, Krska SW, Njolito E, Rivera NR, Sun Y, Rosner T, and Clausen AM. inventors; Patent WO  2006/082251 A1. 
  • 16c Hansen KB. Rosner T. Kubryk M. Dormer PG. Armstrong JD. Org. Lett.  2005,  7:  4935 
    Google Scholar
  • 16d Clausen AM. Dziadul B. Cappuccio KL. Kaba M. Starbuck C. Hsiao Y. Dowling TM. Org. Process Res. Dev.  2006,  10:  723 
    Google Scholar
  • 16e Kubryk M. Hansen KB. Tetrahedron: Asymmetry  2006,  17:  205 
    Google Scholar
  • 17 Dai Q. Yang W. Zhang X. Org. Lett.  2005,  7:  5343 
    CrossrefPubMedGoogle Scholar
  • 18a Bunlaksananusorn T. Rampf F. Synlett  2005,  2682 
    Google Scholar
  • 18b Matsumara K, and Saito K. inventors; World Patent WO  2005/028419. 
  • 19a Vohra RK. Renaud J.-L. Bruneau C. Collect. Czech. Chem. Commun.  2005,  70:  1943 
    Google Scholar
  • 19b Hebbache H. Hank Z. Boutamine S. Meklati M. Bruneau C. Renaud J.-L. C. R. Chim.  2008,  612 
    Google Scholar
  • 21 Vohra RK. Renaud J.-L. Bruneau C. Synthesis  2007,  731 
    Artikel in Thieme ConnectGoogle Scholar
20

It was reported that trifluoroethanol was the best solvent for the hydrogenation of enamino esters and β-N-arylenamino esters in the presence of rhodium catalysts; see references 15 and 16.