Download PDF
Synlett 2011(7): 1000-1004  
DOI: 10.1055/s-0030-1259709
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Phosphine-Catalyzed [3+2] Cycloadditions of 2-Phenyl-4-Arylidene-5(4H)-Oxazolones with Allenoate: A Concise Synthesis of Aspartic Acid Analogues

You-Quan Zou, Chao Li, Jian Rong, Hao Yan, Jia-Rong Chen*, Wen-Jing Xiao*
Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. of China
Fax: +86(27)67862041; e-Mail: wxiao@mail.ccnu.edu.cn;
Further Information

Publication History

Received 17 October 2010
Publication Date:
08 March 2011 (online)

    Permissions and Reprints All articles of this category

Abstract

A Ph3P-catalyzed [3+2] cycloaddition of 2-phenyl-4-arylidene-5(4H)-oxazolones with benzyl 2,3-butadienoate has been developed for the efficient synthesis of structurally diverse and conformationally constrained aspartic acid analogues.

Key words

cycloaddition - organocatalysis - phosphine - benzyl 2,3-butadienoate - aspartic acid analogues

    References and Notes

  • For some recent reviews on this topic, see:
  • 1a Bräuner-Osborne H. Egebjerg J. Nielsen E. Madsen U. Krogsgaard-Larsen P. J. Med. Chem.  2000,  43:  2609 
    Google Scholar
  • 1b Trist DG. Pharm. Acta Helv.  2000,  74:  221 
    Google Scholar
  • 1c Liskamp RMJ. Recl. Trav. Chim. Pays-Bas  1994,  113:  1 
    Google Scholar
  • 1d Goodman M. Shao H. Pure Appl. Chem.  1996,  68:  1303 
    Google Scholar
  • 1e Cativiela C. Díaz-de-Villegas MD. Tetrahedron: Asymmetry  1998,  9:  3517 
    Google Scholar
  • 1f Cativiela C. Díaz-de-Villegas MD. Tetrahedron: Asymmetry  2000,  11:  645 
    Google Scholar
  • 1g Andrei M. Römming C. Undheim K. Tetrahedron: Asymmetry  2004,  15:  1359 
    Google Scholar
  • 2a Curry K. Magnuson DSK. McLennan H. Peet MJ. Neurosci. Lett.  1986,  66:  101 
    Google Scholar
  • 2b Peet MJ. Curry K. Magnuson DSK. McLennan H. Neuroscience  1987,  22:  563 
    Google Scholar
  • 2c Curry K. Magnuson DSK. McLennan H. Peet MJ. Can. J. Physiol. Pharmacol.  1987,  65:  2196 
    Google Scholar
  • 3 The Glutamate Receptors   Gereau RW. Swanson GT. Humana Press; Portland / OR: 2008. 
    Google Scholar
  • 4 Schoepp DD. Jane DE. Monn JA. Neuropharmacology  1999,  38:  1431 
    CrossrefGoogle Scholar
  • 5a Jayaraman V. Keesey R. Madden DR. Biochemistry  2000,  39:  8693 
    Google Scholar
  • 5b Bessis AS. Jullian N. Coudert E. Pin JP. Acher F. Neuropharmacology  1999,  38:  1543 
    Google Scholar
  • 6a Ornstein PL. Schoepp DD. Monn JA. Curr. Pharm. Des.  1995,  1:  355 
    Google Scholar
  • 6b Jullian N. Brabet I. Pin JP. Acher FC. J. Med. Chem.  1999,  42:  1546 
    Google Scholar
  • 6c Bertrand HO. Bessis AS. Pin JP. Acher FC.
    J. Med. Chem.  2002,  45:  3171 
    Google Scholar
  • For a recent comprehensive review on the stereoselective synthesis of cyclic quaternary α-amino acids see:
  • 7a Cativiela C. Ordóñez M. Tetrahedron: Asymmetry  2009,  20:  1 
    Google Scholar
  • For selected examples, see:
  • 7b Pyne SG. Schafer K. Skelton BW. White AH. Chem. Commun.  1997,  2267 
    Google Scholar
  • 7c Ung AT. Schafer K. Lindsay KB. Pyne SG. Amornraska K. Wouters R. Van der Linden I. Biesmans I. Lesage ASJ. Skelton BW. White AH. J. Org. Chem.  2002,  67:  227 
    Google Scholar
  • 7d Pham TQ. Pyne SG. Skelton BW. White AH. Tetrahedron Lett.  2002,  43:  5953 
    Google Scholar
  • 7e Suri JT. Steiner DD. Barbas CF. Org. Lett.  2005,  7:  3885 
    Google Scholar
  • 7f Caputo F. Clerici F. Gelmi ML. Pellegrino S. Pocar D. Tetrahedron: Asymmetry  2006,  17:  1430 
    Google Scholar
  • 7g Jam F. Tullberg M. Luthman K. Grøtli M. Tetrahedron  2007,  63:  9881 
    Google Scholar
  • 7h Conti P. Pinto A. Roda G. Tamborini L. Arosio D. Micheli CD. Synthesis  2007,  2145 
    Google Scholar
  • 7i Avenoza A. Busto JH. Canal N. Corzana F. Peregrina JM. Pérez-Fernández M. Rodríguez F. J. Org. Chem.  2010,  75:  545 
    Google Scholar
  • For reviews on phosphine-catalyzed reactions, see:
  • 8a Lu XY. Zhang CM. Xu ZR. Acc. Chem. Res.  2001,  34:  535 
    Google Scholar
  • 8b Methot JL. Roush WR. Adv. Synth. Catal.  2004,  346:  1035 
    Google Scholar
  • 8c Lu XY. Du YS. Lu C. Pure Appl. Chem.  2005,  77:  1985 
    Google Scholar
  • 8d Nair V. Menon RS. Sreekanth AR. Abhilash N. Biju AT. Acc. Chem. Res.  2006,  39:  520 
    Google Scholar
  • 8e Ye LW. Zhou J. Tang Y. Chem. Soc. Rev.  2008,  37:  1140 
    Google Scholar
  • 8f Cowen BJ. Miller SJ. Chem. Soc. Rev.  2009,  38:  3102 
    Google Scholar
  • 8g Marinetti A. Voituriez A. Synlett  2010,  174 
    Google Scholar
  • 8h Wei Y. Shi M. Acc. Chem. Res.  2010,  43:  1005 
    Google Scholar
  • 9a Zhang CM. Lu XY. Synlett  1995,  645 
    Google Scholar
  • 9b Zhang CM. Lu XY. J. Org. Chem.  1995,  60:  2906 
    Google Scholar
  • 9c Xu Z. Lu XY. Tetrahedron Lett.  1997,  38:  3461 
    Google Scholar
  • 9d Xu Z. Lu XY. J. Org. Chem.  1998,  63:  5031 
    Google Scholar
  • 9e Xu Z. Lu XY. Tetrahedron Lett.  1999,  40:  549 
    Google Scholar
  • 9f Lu XY. Lu Z. Zhang XM. Tetrahedron  2006,  62:  457 
    Google Scholar
  • For recent exmples, see:
  • 10a Lu Z. Zheng SQ. Zhang XM. Lu XY. Org. Lett.  2008,  10:  3267 
    Google Scholar
  • 10b Wallace DJ. Sidda RL. Reamer RA. J. Org. Chem.  2007,  72:  1051 
    Google Scholar
  • 10c Sampath M. Loh TP. Chem. Commun.  2009,  1568 
    Google Scholar
  • 10d Henry CE. Kwon O. Org. Lett.  2007,  9:  3069 
    Google Scholar
  • 10e Shu LH. Sun WQ. Zhang DW. Wu SH. Wu HM. Xu JF. Lao XF. Chem. Commun.  1997,  79 
    Google Scholar
  • 10f O’Donovan BF. Hitchcock PB. Meidine MF. Kroto HW. Taylor R. Walton DRM. Chem. Commun.  1997,  81 
    Google Scholar
  • 10g Dudding T. Kwon O. Mercier E. Org. Lett.  2006,  8:  3643 
    Google Scholar
  • 10h Xia YZ. Liang Y. Chen YY. Wang M. Jiao L. Huang F. Liu S. Li YH. Yu ZX. J. Am. Chem. Soc.  2007,  129:  3470 
    Google Scholar
  • 10i Ruano JLG. Nunez A. Martin MR. Fraile A. J. Org. Chem.  2008,  73:  9366 
    Google Scholar
  • 10j Kumar K. Kapoor R. Kapur A. Ishar MPS. Org. Lett.  2000,  2:  2023 
    Google Scholar
  • 10k Pham TQ. Pyne SG. Skelton BW. White AH. J. Org. Chem.  2005,  70:  6369 
    Google Scholar
  • 10l Zhu GX. Chen ZG. Jiang QZ. Xiao DP. Cao P. Zhang XM. J. Am. Chem. Soc.  1997,  119:  3836 
    Google Scholar
  • 10m Wilson J. Fu GC. Angew. Chem. Int. Ed.  2006,  45:  1426 
    Google Scholar
  • 10n Cowen BJ. Miller SJ. J. Am. Chem. Soc.  2007,  129:  10988 
    Google Scholar
  • 10o Voituriez A. Panossian A. Fleury-Brégeot N. Retailleau P. Marinetti A. J. Am. Chem. Soc.  2008,  130:  14030 
    Google Scholar
  • 10p Xiao H. Chai Z. Zheng CW. Yang YQ. Liu W. Zhang JK. Zhao G. Angew. Chem. Int. Ed.  2010,  49:  4467 
    Google Scholar
  • 10q Voituriez A. Pinto N. Neel M. Retailleau P. Marinetti A. Chem. Eur. J.  2010,  16:  12541 
    Google Scholar
  • 10r Pinto N. Neel M. Panossian A. Retailleau P. Frison G. Voituriez A. Marinetti A. Chem. Eur. J.  2010,  16:  1033 
    Google Scholar
  • 10s Guan XY. Wei Y. Shi M. Org. Lett.  2010,  12:  5024 
    Google Scholar
  • 11a Lu HH. Zhang FG. Meng XG. Duan SW. Xiao WJ. Org. Lett.  2009,  11:  3946 
    Google Scholar
  • 11b Li CF. Liu H. Liao J. Cao YJ. Liu XP. Xiao WJ. Org. Lett.  2007,  9:  1847 
    Google Scholar
  • 11c Lu HH. Liu H. Wu W. Wang XF. Lu LQ. Xiao WJ. Chem. Eur. J.  2009,  15:  2742 
    Google Scholar
  • 11d Lu LQ. Cao YJ. Liu XP. An J. Yao CJ. Ming ZH. Xiao WJ. J. Am. Chem. Soc.  2008,  130:  6946 
    Google Scholar
  • 11e Chen JR. Li CF. An XL. Zhang JJ. Zhu XY. Xiao WJ. Angew. Chem. Int. Ed.  2008,  47:  2489 
    Google Scholar
  • 11f Lu LQ. Li F. An J. Zhang JJ. An XL. Hua QL. Xiao WJ. Angew. Chem. Int. Ed.  2009,  48:  9542 
    Google Scholar
  • 11g Lu LQ. Zhang JJ. Li F. An J. Hua QL. Chen JR. Xiao WJ. Angew. Chem. Int. Ed.  2010,  49:  4495 
    Google Scholar
  • 11h An XL. Chen JR. Li CF. Zhang FG. Zou YQ. Guo YC. Xiao WJ. Chem. Asian J.  2010,  5:  2258 
    Google Scholar
  • 11i Wang XF. Hua QL. Cheng Y. An XL. Yang QQ. Chen JR. Xiao WJ. Angew. Chem. Int. Ed.  2010,  49:  8379 
    Google Scholar
  • 12 For the preparation of compounds 6, see: Herbst RM. Shemin D. Org. Synth., Coll. Vol. II   John Wiley and Sons; London: 1943.  p.1 
    Google Scholar
  • For selected examples, see:
  • 15a Guo RW. Morris RH. Song DT. J. Am. Chem. Soc.  2005,  127:  516 
    Google Scholar
  • 15b Abdur-Rashid K. Guo RW. Lough AJ. Morris RH. Song DT. Adv. Synth. Catal.  2005,  347:  571 
    Google Scholar
  • 15c Kawamura K. Fukuzawa H. Hayashi M. Org. Lett.  2008,  10:  3509 
    Google Scholar
  • 15d Boeda F. Rix D. Clavier H. Crévisy C. Mauduit M. Tetrahedron: Asymmetry  2006,  17:  2726 
    Google Scholar
  • 15e Lam H. Horton PN. Hursthouse MB. Aldous DJ. Hii KK. Tetrahedron Lett.  2005,  46:  8145 
    Google Scholar
13

The configuration of 7a was determined by X-ray crystallographic analysis. CCDC 783340 (7a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

14

The relative stereochemistry of 10a was assigned by the coupling constants and NOE analysis of its NMR spectra, see the Supporting Information.