Synthesis 2018; 50(03): 607-616
DOI: 10.1055/s-0036-1590945
paper
© Georg Thieme Verlag Stuttgart · New York

Economical Synthesis of α-Amino Acids from a Novel Family of Easily Available Schiff Bases of Glycine Esters and 2-Hydroxy­benzophenone

Zalina T. Gugkaeva
a   A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   eMail: yubel@ineos.ac.ru
,
a   A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   eMail: yubel@ineos.ac.ru
b   Department of Inorganic Chemistry, People’s Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, 117198 Moscow, Russian Federation
,
Margarita A. Moskalenko
a   A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   eMail: yubel@ineos.ac.ru
,
Victor N. Khrustalev
b   Department of Inorganic Chemistry, People’s Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, 117198 Moscow, Russian Federation
,
Yulia V. Nelyubina
a   A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   eMail: yubel@ineos.ac.ru
,
Alexander S. Peregudov
a   A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   eMail: yubel@ineos.ac.ru
,
Alan T. Tsaloev
c   Chemical Diversity Research Institute, 2a Rabochaya Street, 141400 Khimki, Moscow Region, Russian Federation
,
Victor I. Maleev
a   A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   eMail: yubel@ineos.ac.ru
,
Yuri N. Belokon*
a   A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   eMail: yubel@ineos.ac.ru
› Institutsangaben
This work was supported by the Russian Science Foundation (RSF grant 17-73-10016). X-ray studies were supported by the RUDN University Program 5-100.
Weitere Informationen

Publikationsverlauf

Received: 07. September 2017

Accepted after revision: 07. Oktober 2017

Publikationsdatum:
09. November 2017 (online)


Abstract

We report a novel, efficient, and easily prepared substrate/precursor family of Schiff bases of various glycine esters with 2-hydroxybenzophenone, and their use for the synthesis of amino acids in quantitative yields. The Michael addition of the substrates to methyl acrylate gave two different types of product (cyclic or chain), depending on the nature of the base. Also, we demonstrated that one of the new substrates could be involved in an asymmetric version of the alkylation reaction (70% ee).

Supporting Information

 
  • References

  • 1 Breuer M. Ditrich K. Habicher T. Hauer B. Keßeler M. Stürmer R. Zelinski T. Angew. Chem. Int. Ed. 2004; 43: 788
    • 2a Walsh CT. Garneau-Tsodikova S. Gatto GJ. Jr. Angew. Chem. Int. Ed. 2005; 44: 7342
    • 2b Hanessian S. Auzzas L. Acc. Chem. Res. 2008; 41: 1241
    • 2c Ngo JT. Tirrell DA. Acc. Chem. Res. 2011; 44: 677
    • 2d Boutureira O. Bernardes GJ. L. Chem. Rev. 2015; 115: 2174
    • 3a Blaser H.-U. Chem. Rev. 1992; 92: 935
    • 3b Sardina FJ. Rapoport H. Chem. Rev. 1996; 96: 1825
    • 3c Kazmaier U. Angew. Chem. Int. Ed. 2005; 44: 2186
    • 3d Davie EA. C. Mennen SM. Xu Y. Miller SJ. Chem. Rev. 2007; 107: 5759
  • 4 Asymmetric Synthesis and Application of α-Amino Acids. Soloshonok VA. Izawa K. American Chemical Society; Washington DC: 2009

    • For selected reviews on asymmetric synthesis of amino acids, see:
    • 5a Duthaler RO. Tetrahedron 1994; 50: 1539
    • 5b Cativiela C. Díaz-de-Villegas MD. Tetrahedron: Asymmetry 1998; 9: 3517
    • 5c Cativiela C. Díaz-de-Villegas MD. Tetrahedron: Asymmetry 2000; 11: 645
    • 5d Taggi AE. Hafez AM. Lectka T. Acc. Chem. Res. 2003; 36: 10
    • 5e Ma J.-A. Angew. Chem. Int. Ed. 2003; 42: 4290
    • 5f Nájera C. Sansano JM. Chem. Rev. 2007; 107: 4584
    • 6a O’Donnell MJ. Eckrich TM. Tetrahedron Lett. 1978; 19: 4625
    • 6b O’Donnell MJ. Polt RL. J. Org. Chem. 1982; 47: 2663
    • 6c O’Donnell MJ. Bennett WD. Bruder WA. Jacobsen WN. Knuth K. LeClef B. Polt RL. Bordwell FG. Mrozack SR. Cripe TR. J. Am. Chem. Soc. 1988; 110: 8520
    • 7a O’Donnell MJ. Delgado F. Hostettler C. Schwesinger R. Tetrahedron Lett. 1998; 39: 8775
    • 7b O’Donnell MJ. Acc. Chem. Res. 2004; 37: 506

      For selected reviews on the use of the O’Donnell Schiff base in asymmetric catalysis, see:
    • 8a O’Donnell MJ. Aldrichimica Acta 2001; 34: 3
    • 8b Maruoka K. Ooi T. Chem. Rev. 2003; 103: 3013
    • 8c Lygo B. Andrews BI. Acc. Chem. Res. 2004; 37: 518
    • 8d Hashimoto T. Maruoka K. Chem. Rev. 2007; 107: 5656
    • 8e Maruoka K. Ooi T. Kano T. Chem. Commun. 2007; 1487
    • 8f Maruoka K. Chem. Rec. 2010; 10: 254
    • 8g Shirakawa S. Maruoka K. Angew. Chem. Int. Ed. 2013; 52: 4312

      For selected recent examples of the use of O’Donnell Schiff base in asymmetric catalysis, see:
    • 9a Itsuno S. Paul DK. Salam MA. Haraguchi N. J. Am. Chem. Soc. 2010; 132: 2864
    • 9b Kano T. Kumano T. Sakamoto R. Maruoka K. Chem. Sci. 2010; 1: 499
    • 9c Denmark SE. Gould ND. Wolf LM. J. Org. Chem. 2011; 76: 4260
    • 9d Ma T. Fu X. Kee CW. Zong L. Pan Y. Huang K.-W. Tan C.-H. J. Am. Chem. Soc. 2011; 133: 2828
    • 9e Nun P. Pérez V. Calmès M. Martinez J. Lamaty F. Chem. Eur. J. 2012; 18: 3773
    • 9f Shirakawa S. Liu Y. Usui A. Maruoka K. ChemCatChem 2012; 4: 980
    • 9g Sheshenev AE. Boltukhina EV. White AJ. P. Hii KK. Angew. Chem. Int. Ed. 2013; 52: 6988
    • 9h Belokon YN. Maleev VI. North M. Larionov VA. Savelyeva TF. Nijland A. Nelyubina YV. ACS Catal. 2013; 3: 1951
    • 9i de Freitas Martins E. Rodriguez Pliego JJr. ACS Catal. 2013; 3: 613
    • 9j Maleev VI. North M. Larionov VA. Fedyanin IV. Savel’yeva TF. Moscalenko MA. Smolyakov AF. Belokon YN. Adv. Synth. Catal. 2014; 356: 1803
    • 9k Tiffner M. Novacek J. Busillo A. Gratzer K. Massa A. Waser M. RSC Adv. 2015; 5: 78941
    • 9l Liu B. Zhang Z.-M. Xu B. Xu S. Wu H.-H. Liu Y. Zhang J. Org. Chem. Front. 2017; 4: 1772
  • 10 The Aldrich catalogue number for O’Donnell’s substrate is 364487-1G [catalogue name: N-(diphenylmethylene)glycine tert-butyl ester].
  • 11 Pickard PL. Tolbert TL. Org. Synth. Coll. Vol. V . Wiley; London: 1973: 520
  • 12 Ooi T. Arimura Y. Hiraiwa Y. Yuan LM. Kano T. Inoue T. Matsumoto J. Maruoka K. Tetrahedron: Asymmetry 2006; 17: 603
    • 13a Li K. Tan G. Huang J. Song F. You J. Angew. Chem. Int. Ed. 2013; 52: 12942
    • 13b Przybyla D. Nubbemeyer U. Eur. J. Org. Chem. 2017; 695
  • 14 Martell AE. Adv. Enzymol. Relat. Areas Mol. Biol. 1982; 53: 163
  • 15 The structure of the adduct 5c {tert-butyl (2R*,3aR*,9bR*)-4-oxo-9b-phenyl-1,2,3,3a,4,9b-hexahydrochromeno[4,3-b]pyrrole-2-carboxylate} was determined by single-crystal X-ray analysis (see Supporting Information, Figure S2).
  • 16 O’Donnell MJ. Delgado F. Domínguez E. de Blas J. Scott WL. Tetrahedron: Asymmetry 2001; 12: 821
  • 17 Corey EJ. Xu F. Noe MC. J. Am. Chem. Soc. 1997; 119: 12414
  • 18 Trivedi TJ. Rao KS. Singh T. Mandal SK. Sutradhar N. Panda AB. Kumar A. ChemSusChem 2011; 4: 604
  • 19 Zeng D. Zhang R. Nie Q. Cao L. Shang L. Yin Z. ACS Med. Chem. Lett. 2016; 7: 1197
  • 20 Krause L. Herbst-Irmer R. Sheldrick GM. Stalke D. J. Appl. Crystallogr. 2015; 48: 3
  • 21 Evans PR. Acta Crystallogr., Sect. D 2006; 62: 72
  • 22 Battye TG. G. Kontogiannis L. Johnson O. Powell HR. Leslie AG. W. Acta Crystallogr., Sect. D 2011; 67: 271
  • 23 Sheldrick GM. Acta Crystallogr., Sect. C 2015; 71: 3
  • 24 CCDC 1544856 (2b), 1544857 (3ba), 1533795 (4bg), 1533796 (5b), and 1533797 (5c) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.