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Synlett 2011(7): 992-994  
DOI: 10.1055/s-0030-1259711
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Brønsted Acid Catalyzed Dynamic Kinetic Resolution of Azlactones for the Synthesis of Aryl Glycine Derivatives

Chao Wang, Hong-Wen Luo, Liu-Zhu Gong*
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China
Fax: +86(551)3606266; e-Mail: gonglz@ustc.edu.cn;
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Publication History

Received 30 January 2011
Publication Date:
08 March 2011 (online)

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Abstract

The dynamic kinetic resolution of C4-aryl azlactones with alcohols was investigated by employing Brønsted acid catalysis. The reaction provided an efficient complementary approach to access chiral aryl glycine derivatives with excellent yields (up to 99%) and enantioselectivities (up to 96% ee).

Key words

dynamic kinetic resolution - azlactone - aryl glycine - Brønsted acid - amino acid

    References

  • For some representative applications, see, for example:
  • 1a Lu Y. Johnstone TC. Arndtsen BA. J. Am. Chem. Soc.  2009,  131:  11284 
    Google Scholar
  • 1b Kazmaier U. Angew. Chem. Int. Ed.  2005,  44:  2186 
    Google Scholar
  • 1c Sardina JF. Rapoport H. Chem. Rev.  1996,  96:  1825 
    Google Scholar
  • For reviews, see:
  • 2a Nájera C. Sansano JM. Chem. Rev.  2007,  107:  4584 
    Google Scholar
  • 2b Ma J.-A. Angew. Chem. Int. Ed.  2003,  42:  4290 
    Google Scholar
  • 3a Brown JM. In Comprehensive Asymmetric Catalysis   Vol. 1:  Jacobsen EN. Pfaltz A. Yamamoto H. Springer; Berlin: 1999.  Chap. 5.1.
    Google Scholar
  • 3b Noyori R. Asymmetric Catalysis in Organic Synthesis   Wiley; New York: 1994.  Chap. 2.
    Google Scholar
  • 3c Tang W. Zhang X. Chem. Rev.  2003,  103:  3029 
    Google Scholar
  • 4a Rama Rao AV. Gurjar MK. Laxma Reddy K. Rao AS. Chem. Rev.  1995,  95:  2135 
    Google Scholar
  • 4b Meyer EM. Boesten WHJ. Schoemaker HE. van Balken JAM. In Biocatalysis in Synthesis   Tramper J. van der Plas HC. Linko P. Elsevier; Amsterdam: 1985.  p.135-158  
    Google Scholar
  • 4c Townsend CA. Brown AM. J. Am. Chem. Soc.  1983,  105:  913 
    Google Scholar
  • 4d Spencer JL. Flynn EH. Roeske RW. Siu FY. Chauvette RR. J. Med. Chem.  1966,  9:  746 
    Google Scholar
  • For recent examples, see:
  • 5a Li G. Liang Y. Antilla JC. J. Am. Chem. Soc.  2006,  128:  6304 
    Google Scholar
  • 5b Shang G. Yang Q. Zhang X. Angew. Chem. Int. Ed.  2006,  45:  6360 
    Google Scholar
  • 5c Beenen MA. Weix DJ. Ellman JA. J. Am. Chem. Soc.  2006,  128:  6304 
    Google Scholar
  • 5d Shirakawa S. Berger R. Leighton JL. J. Am. Chem. Soc.  2005,  127:  2858 
    Google Scholar
  • 5e Sigman MS. Vachal P. Jacobsen EN. Angew. Chem. Int. Ed.  2000,  39:  1279 
    Google Scholar
  • 5f Krueger CA. Kuntz KW. Dzierba CD. Wirschun WG. Gleason JD. Snapper ML. Hoveyda AH. J. Am. Chem. Soc.  1999,  121:  4284 
    Google Scholar
  • 5g Saaby S. Fang X. Gathergood N. Jorgensen KA. Angew. Chem. Int. Ed.  2000,  39:  4114 
    Google Scholar
  • 5h For a review on asymmetric arylglycine syntheses, see: Williams RM. Hendrix JA. Chem. Rev.  1992,  92:  889 
    Google Scholar
  • 6 For a review of azlactone chemistry, see: Fisk JS. Mosey RA. Tepe JJ. Chem. Soc. Rev.  2007,  36:  1432 
    CrossrefPubMedGoogle Scholar
  • 7 Pellissier H. Tetrahedron  2008,  64:  1563 
    CrossrefPubMedGoogle Scholar
  • 8a Crich JZ. Brieva R. Marquart P. Gu RL. Flemming S. Sih CJ. J. Org. Chem.  1993,  58:  3252 
    Google Scholar
  • 8b Brown SA. Parker M.-C. Turner NJ. Tetrahedron: Asymmetry  2000,  11:  1687 ; and references cited therein
    Google Scholar
  • 9a Seebach D. Jaeschke G. Gottwald K. Mastsuda K. Formisano R. Chaplin DA. Breuning M. Bringmann G. Tetrahedron  1997,  53:  7539 
    Google Scholar
  • 9b Gottwald K. Seebach D. Tetrahedron  1999,  55:  723 
    Google Scholar
  • 10a Liang J. Ruble JC. Fu GC. J. Org. Chem.  1998,  63:  3154 
    Google Scholar
  • 10b Xie L. Hua W. Chan ASC. Leung Y.-C. Tetrahedron: Asymmetry  1999,  10:  4715 
    Google Scholar
  • 10c Berkessel A. Cleeman F. Mukherjee S. Müller TN. Lex J. Angew. Chem. Int. Ed.  2005,  44:  807 
    Google Scholar
  • 10d Peschiulli A. Quigley C. Tallon S. Gun’ko YK. Connon SJ. J. Org. Chem.  2008,  73:  6409 
    Google Scholar
  • 10e Yang X. Lu G. Birman VB. Org. Lett.  2010,  12:  892 
    Google Scholar
  • 11 Jiang J. Qing J. Gong L.-Z. Chem. Eur. J.  2009,  15:  7031 
    CrossrefPubMedGoogle Scholar
  • 12a Li G. Fronczek FR. Atilla JC. J. Am. Chem. Soc.  2008,  130:  12216 
    Google Scholar
  • 12b Gu Q. Rong Z.-Q. Zheng C. You S.-L. J. Am. Chem. Soc.  2010,  132:  4056 
    Google Scholar
  • 12c Čorić I. Vellalath S. List B. J. Am. Chem. Soc.  2010,  132:  8536 
    Google Scholar
  • 12d Čorić I. Müller S. List B. J. Am. Chem. Soc.  2010,  132:  17370 
    Google Scholar
  • 13a Akiyama T. Chem. Rev.  2007,  107:  5744 
    Google Scholar
  • 13b Terada M. Chem. Commun.  2008,  4097 
    Google Scholar
  • 13c Doyle AG. Jacobsen EN. Chem. Rev.  2007,  107:  5713 
    Google Scholar
  • 14 During the preparation of this manuscript, Birman and co-workers reported a Brønsted acid catalyzed dynamic kinetic resolution of azlactones, see: Lu G. Birman VB. Org. Lett.  2011,  13:  356 
    CrossrefGoogle Scholar