Synthesis of chiral spiro 3-oxazolin-5-one 3-oxides (Chiral nitrones) via a nitrosoketene intermediate and their asymmetric 1,3-dipolar cycloaddition reactions leading to the EPC synthesis of modified amino acids,

Tetrahedron

Volumn 53, Issue 16, 1997, Pages 5725-5746

  Katagiri, Nobuya ^a   Okada, Makoto ^a   Morishita, Yoshihiro ^a   Kaneko, Chikara ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLGLYCINE; AMINO ACID DERIVATIVE; CYCLOPENTENYLGLYCINE; OXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CHIRALITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030906038     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00284-6     Document Type: Article

References (27)

1. Gong, L.; McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1991, 113, 6021.
2. McAllister, M. A.; Tidwell, T. T. J. Org. Chem. 1994, 59, 4506.
3. Tidwell, T. T. Ketenes; John Wiley & Sons: New York, 1995.
4. Very recently, we have detected nitrosoketene (2) generated by pyrolysis of 1 using FT-IR spectroscopy. Matsui, H.; Zuckerman, E. J.; Katagiri, N.; Kaneko, C.; Ham, S.; Birney, D. M. J. Phys. Chem. in press.
5. Katagiri, N.; Kurimoto, A.; Yarnada, A.; Sato, H.; Katsuhara, T.; Takagi, K.; Kaneko, C. J. Chem. Soc., Chem. Commun. 1994, 281.
6. Katagiri, N.; Sato, H.; Kurimoto, A.; Okada, M.; Yamada, A.; Kaneko, C. J. Org. Chem. 1994, 59, 8101.
7. Ham, S.; Birney, D. M. Tetrahedron Lett. 1994, 35, 8113.
8. For a recent review dealing with the stereoselective synthesis of α-amino acids, see: Duthaler, R. O. Tetrahedron, 1994, 50, 1539.
9. Katagiri, N.; Okada, M.; Kaneko, C. Tetrahedron Lett. 1996, 37, 1801.
10. Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. J. Chem. Soc., Chem. Commun. 1996, 2137.
11. In this reaction, the other isomer (more polar than 5) was also obtained in 14% yield, which would be formed by the reaction of 2 with isomenthone being contained as an impurity.
12. 4 from less hindered side (lower side) to give the 3,5-cis product D.
13. DeShong, P.; Dicken, C. M.; Staib, R. R.; Freyer, A. J.; Weinreb, S. M. J. Org. Chem. 1982, 47, 4397.
14. 6 However, it seems reasonable to assume that the product is the exo-adduct.
15. For recent papers dealing with the synthesis of optically active allylglycine, see: (a) Oppolzer, W.; Moretti, R.; Zhou, C. Helv. Chim. Acta. 1994, 77, 2363;
16. (b) Rose, J. E.; Leeson, P. D.; Gani, D. J. Chem. Soc. Perkin Trans. 1. 1995, 157. In both references, the amino acids were synthesized by the allylation of chiral glycine derivatives in the presence of butyl lithium followed by appropriate manipulations.
17. Dennis, R. L.; Plent, W. J.; Skinner, C. G.; Sutherland, G. L.; Shire, W. J. Am. Chem. Soc. 1995, 77, 2362.
18. Cramer, V.; Spener, F. Eur. J. Biochm. 1977, 74, 495.
19. 19 to the best of our knowledge, the asymmetric cycloaddition involving kinetical resolution of the dipolarophile is hitherto unknown.
20. Recent papers dealing with the 1,3-dipolar cycloaddition of nitrones in the presence of Lewis acid catalyst: (a) Murahashi, S.-I.; Imada, Y.; Kohno, M.; Kawakami, T. Synlett. 1993, 395;
21. (b) Tamura, O.; Yamaguchi, T.; Noe, K.; Sakamoto, M. Tetrahedron Lett. 1993, 34, 4009.
22. (c) Gothelf, K. V.; Jorgensen, K. A. J. Org. Chem. 1994, 59, 5687;
23. (d) Kanemasa, S.; Tsuruoka, T.; Yamamoto, H. Tetrahedron Lett. 1995, 36, 5019;
24. (e) Seerden, J.-P. G.; Kuypers, M. M. M.; Scheeren, H. W. Tetrahedron: Asymmetry, 1995, 6, 1441.
25. Cramer, V.; Rehfeldt, A. G.; Spener, F. Biochemistry, 1980, 19, 3074.
26. Williams, R. M.; Sinclair, P.J.; D. Zhai, D.; Chen, D. J. Am. Chem. Soc. 1988, 110, 1547.
27. Black, S.; Wright, N. G. J. Biol. Chem. 1955, 213, 39.