DOI QR코드

DOI QR Code

L-Lactate-mediated Dynamic Kinetic Resolution of α-Bromo Esters for Asymmetric Syntheses of α-Amino Acid Derivatives

  • Kim, Yelim (Department of Chemistry and KFnSC, Konkuk University) ;
  • Park, Kon Ji (Department of Chemistry and KFnSC, Konkuk University) ;
  • Choi, Yun Soo (Department of Chemistry and KFnSC, Konkuk University) ;
  • Lee, Myung-Su (Department of Chemistry and KFnSC, Konkuk University) ;
  • Park, Yong Sun (Department of Chemistry and KFnSC, Konkuk University)
  • Received : 2013.04.22
  • Accepted : 2013.05.24
  • Published : 2013.08.20

Abstract

Keywords

References

  1. Park, Y. S. Tetrahedron: Asymmetry 2009, 43, 8253.
  2. Devine, P. N.; Dolling, U.-H.; Heid, R. M.; Tschaen, D. M. Tetrahedron Lett. 1996, 37, 2683. https://doi.org/10.1016/0040-4039(96)00391-7
  3. Devine, P. N.; Heid, R. M.; Tschaen, D. M. Tetrahedron 1997, 53, 6739. https://doi.org/10.1016/S0040-4020(97)00325-6
  4. Devine, P. N.; Foster, B. S.; Grabowski, E. J. J.; Reider, P. J. Heterocycles 2002, 58, 119. https://doi.org/10.3987/COM-02-S(M)54
  5. Ammazzalorso, A.; Amoroso, R.; Bettoni, G.; De Filippis, B.; Giampietro, L.; Maccallini, C.; Tricca, M. L. Arkivoc 2004, 375.
  6. Ammazzalorso, A.; Amoroso, R.; Bettoni, G.; De Filippis, B.; Fantacuzzi, M.; Giampietro, L.; Maccallini, C.; Tricca, M. L. Eur. J. Org. Chem. 2006, 4088.
  7. Koh, K.; Ben, R. N.; Durst, T. Tetrahedron Lett. 1993, 34, 4473. https://doi.org/10.1016/0040-4039(93)88062-N
  8. Jang, J. I.; Kang, S. Y.; Kang, K. H.; Park, Y. S. Tetrahedron 2011, 67, 6221. https://doi.org/10.1016/j.tet.2011.06.055
  9. Kim, Y.; Lee, M. H.; Choi, E. T.; No, E. S.; Park, Y. S. Heterocycles 2007, 71, 5. https://doi.org/10.3987/COM-06-10910
  10. Lee, Y. M.; Park, Y. S. Heterocycles 2009, 78, 2233. https://doi.org/10.3987/COM-09-11700
  11. Kim, Y.; Kang, K. H.; Choi, E. T.; Lee, M. H.; Park, Y. S. Bull. Korean Chem. Soc. 2007, 28, 325. https://doi.org/10.5012/bkcs.2007.28.2.325
  12. Tanimori, S.; Kashiwagi, H.; Nishimura, T.; Kirihata, M. Adv. Synth. Catal. 2010, 352, 2531. https://doi.org/10.1002/adsc.201000323
  13. Rueping, M.; Tato, F.; Schoepke, F. R. Chem. Eur. J. 2010, 16, 2688. https://doi.org/10.1002/chem.200902907
  14. Jiang, Q.; Jiang, D.; Jiang, Y.; Fu, H.; Zhao, Y. Synlett. 2007, 1836.
  15. Abraham, C.; Paull, D. H.; Scerba, M. T.; Grebinski, J. W.; Lectka, T. J. Am. Chem. Soc. 2006, 128, 13370. https://doi.org/10.1021/ja065754d
  16. Mahaney, P. E.; Webb, M. B.; Ye, F.; Sabatucci, J. P.; Steffan, R. J.; Chadwick, C. C.; Harnish, D. C.; Trybulski, E. J. Bioorg. Med. Chem. 2006, 14, 3455. https://doi.org/10.1016/j.bmc.2006.01.001
  17. Chen, Q.-A.; Chen, M.-W.; Yu, C.-B.; Shi, L.; Wang, D.- S.; Yang, Y.; Zhou, Y.-G. J. Am. Chem. Soc. 2011, 133, 16432. https://doi.org/10.1021/ja208073w
  18. Xue, Z.-Y.; Jiang, Y.; Peng, X.-Z.; Yuan, W.-C.; Zhang, X.-M. Adv. Synth. Catal. 2010, 352, 2132. https://doi.org/10.1002/adsc.201000274
  19. Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem. Int. Ed. 2006, 45, 6751. https://doi.org/10.1002/anie.200601832
  20. Storer, R. I.; Carrera, D. E.; Ni, Y.; MacMillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84. https://doi.org/10.1021/ja057222n
  21. Misawa, K.; Suzuki, Y.; Takahashi, S.; Yoshimori, A.; Takasawa, R.; Shibuya, Y.; Tanuma, S. Bioorg. Med. Chem. 2011, 19, 5935. https://doi.org/10.1016/j.bmc.2011.08.064
  22. Godet, T.; Bonvin, Y.; Vincent, G.; Merle, D.; Thozet, A.; Ciufolini, M. A. Organic Lett. 2004, 6, 3281. https://doi.org/10.1021/ol048850x
  23. Lee, M.; Kim, D. H. Bull. Korean Chem. Soc. 2001, 22, 1236.
  24. Insaf, S. S.; Witiak, D. T. Tetrahedron 2000, 56, 2359. https://doi.org/10.1016/S0040-4020(00)00103-4
  25. Chang, J.-Y.; Shin, E.-K.; Kim, H. J.; Kim, Y.; Park, Y. S. Bull. Korean Chem. Soc. 2005, 26, 989. https://doi.org/10.5012/bkcs.2005.26.6.989
  26. Kim, H. J.; Kim, Y.; Choi, E. T.; Lee, M. H.; No, E. S.; Park, Y. S. Tetrahedron 2006, 62, 6303. https://doi.org/10.1016/j.tet.2006.04.045

Cited by

  1. Synthesis of nitromethyl-, N-methylindolyl-, or N-methylindolylnitromethyl-substituted 1,4-benzothiazin(diazin)ones and 3-methyl-1,4-benzoxazinones from alkyl 3-nitroacrylates vol.54, pp.7, 2018, https://doi.org/10.1007/s10593-018-2339-2
  2. Asymmetric Synthesis of Both Diastereomers of α,α′-disubstituted Iminodiacetic Acid Derivatives Using Stereoselective Nucleophilic Substitution of α-Bromo Esters vol.39, pp.5, 2018, https://doi.org/10.1002/bkcs.11446
  3. Iron- or Zinc-Mediated Synthetic Approach to Enantiopure Dihydroquinoxalinones vol.2019, pp.6, 2018, https://doi.org/10.1002/ejoc.201801639
  4. Enantioselective synthesis of trifluoromethylated dihydroquinoxalinones via palladium-catalyzed hydrogenation vol.6, pp.6, 2013, https://doi.org/10.1039/c8qo01361f