Asymmetric synthesis of β-amino acids by addition of chiral enolates to N-Acyloxyiminium ions and application for synthesis of optically active 5-substituted 8-methylindolizidines

Organic Letters

Volumn 1, Issue 1, 1999, Pages 107-110

  Kawakami, Toru ^a   Ohtake, Hiroaki ^a,b   Arakawa, Hiroaki ^a   Okachi, Takahiro ^a   Imada, Yasushi ^a   Murahashi, Shun Ichi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000051598     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9905755     Document Type: Article

References (26)

1. Recent reports for asymmetric synthesis of nitrogen-containing biologically active compounds utilizing diastereoselective addition of nucleophiles to chiral nitrones are given in the following. (a) (+)-Zileuton: Basha, A.; Henry, R.; McLaughlin, M. A.; Ratajczyk, J. D.; Wittenberger, S. J. J. Org. Chem. 1994, 59, 6103-6106.
2. (b) Amino sugars: Dondoni, A.; Franco, S.; Junquera, F.; Merchán, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem. Eur. J. 1995, 1, 505-520.
3. (c) (+)-Lentiginosine: Giovannini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1995, 60, 5706-5707.
4. (d) (+)-Polyoxin J: Dondoni, A.; Franco, S.; Junquera, F.; Merchán, F. L.; Merino, P.; Tejero, T. J. Org. Chem. 1997, 62, 5497-5507.
5. (a) Breuer, E. In The Chemistry of Amino, Nitroso and Nitro Compounds and Their Derivatives, Part 1; Patai, S., Ed.; Wiley: New York, 1982; pp 459-564.
6. (b) Torsell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: Weinheim, 1988.
7. (a) Murahashi, S.-I., Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S. J. Org. Chem. 1990, 55, 1736-1744.
8. (b) Murahashi, S.-I.; Shiota, T.; Imada, Y. Org. Synth. 1992, 70, 265-271.
9. (c) Murahashi, S.-I.; Shiota, T. Tetrahedron Lett. 1987, 28, 2383-2386.
10. (d) Murahashi, S.-I.; Imada, Y.; Ohtake, H. J. Org. Chem. 1994, 59, 6170-6172.
11. Heine, H. W.; Zibuck, R.; VandenHeuvel, W. J. A. J. Am. Chem. Soc. 1982, 104, 3691-3694 and references therein.
12. Coates, R. M.; Cummins, C. H. J. Org. Chem. 1986, 51, 1383-1389.
13. For a review, see: Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1996.
14. For reviews, see: (a) Drey, C. N. C. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: London, 1985; pp 25-54.
15. (b) Griffith, O. W. Annu. Rev. Biochem. 1986, 55, 855-878.
16. For a review, see: Berks, A. H. Tetrahedron 1996, 52, 331-375.
17. Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868-4874.
18. Evans, D. A.; Urpí, F.; Somers, T. C.; Clark, J. S.; Bilodeau, M. T. J. Am. Chem. Soc. 1990, 112, 8215-8216.
19. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129.
20. Examples for the asymmetric synthesis of 5-substituted 8-methylindolizidines: (a) Holmes, A. B.; Smith, A. L.; Williams, S. F.; Hughes, L. R.; Lidert, Z.; Swithendank, C. J. Org. Chem. 1991, 56, 1393-1405.
21. (b) Gnecco, D.; Marazano, C.; Das, B. C. J. Chem. Soc., Chem. Commun. 1991, 625-626.
22. (c) Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876-2883.
23. (d) Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943-945.
24. (e) Comins, D. L.; LaMunyon, D. H.; Chen X. J. Org. Chem. 1997, 62, 8182-8187.
25. (f) Bardou, A.; Célérier, J.-P.; Lhommet, G. Tetrahedron Lett. 1998, 39, 5189-5192.
26. 1H NMR).