Synthesis and Determination of Optical Purity of C2-Symmetric Pyrrolidine Amides as Chiral Auxiliaries

키랄 보조제로서의 C2-대칭성 피롤리딘 아미드의 합성과 광학 순도 결정

  • Moon, Hong-sik (CheilJedang Corporation R&D Center) ;
  • Koh, Dongsoo (Department of Applied Chemistry, Dongduk Women's University)
  • 문홍식 (제일제당 종합연구소) ;
  • 고동수 (동덕여자대학교 응용화학과)
  • Received : 1998.05.27
  • Accepted : 1998.08.02
  • Published : 1998.11.10

Abstract

Optically pure $C_2-Symmetric$ pyrrolidine amides (8) were synthesized from readily available 1,2:5,6-di-O-isopropylidene-D-mannitol (1). Cyclization of dimesylated hexitol (4) with benzyl amine gave an inseparable mixture of $C_2-Symmetric$ pyrrolidine amine derivative (5) as a major product, concurring with its cis isomer (6) as a minor product. The pyrrolidine amines (5,6) were converted to separable pyrrolidine amides (8,9) via free amine (7). Optical purity of desired $C_2-Symmetric$ pyrrolidine amide (8a) was determined with its Mosher derivatives (13,14) by their $^1H$ and $^{19}F$ NMR spectra.

References

  1. J. Org. Chem. v.45 J. K. Whitesell;S. W. Felman
  2. J. Org. Chem. v.54 R. P. Short;R. M. Kennedy;S. J. Masamune
  3. J. Chem. Soc. Chem. Commun v.1024 F. Bjorkling;J. Boutelje;M. Hjalmarsson;K. Hult;T. J. Norin
  4. Tetrahedron Lett v.25 Y. Ito;T. Katsuki;M. Yamaguchi
  5. Tetrahedron v.44 S. Ikegami;T. Katsuki;T. Hayama;T .Uchiyama
  6. Bull. Chem. Soc. Jpn. v.60 Y. Kawanami;T. Katsuki;M. Yamaguchi
  7. Chem. Ltee. v.25 Y. Kawanami;I. Fujita;S. Osawa;T. Katsuki
  8. Tetrahedron Lett v.31 K. Fuji;M. Node;Y. Naniwa;T. Kawabata
  9. J. Org. Chem. v.53 J. K. Whitesell;M. A. Minton;K. M. Chen
  10. Synlett. v.319 Y. Yamamoto;H. Ohmori;S. Sawada
  11. J. Org. Chem. v.42 J. K. Whitesell;S. W. Felman
  12. Tetrahedron Lett. v.25 Y. Kawanami;Y. Ito;T. Kitagawa;Y. Tanicuchi;T. Katsuki;M. Yamaguchi
  13. Tetrahedron Lett. v.30 S. Takano;M. Moriya;Y. Iwabuchi;K. Ogasawara
  14. Tetrahedron Lett. v.30 M. Marzi;D. Misiti
  15. J. Org. Chem. v.55 H. A. Watson;B. T. O'Neal
  16. J. Org. Chem. v.26 S. W. Blackman;R. Baltzly
  17. J. Am. Chem. Soc. v.94 E. J. Corey;A. Venkateswarlu
  18. Synthesis v.472 G. Cainelli;F. Manescalchi
  19. J. Org. Chem. v.54 S. Collins;B. A. Kuntz;Y. Hong
  20. Dynamic Nuclear Magnetic Resonance Spectroscopy L. M. Jackman(Ed.);F. A. Cotton(Ed.)
  21. Dynamic NMR Spectroscopy J. Sandstorm