Reversal of diastereoselectivity of the reaction of chiral boron and titanium enolates with nitrones via N-acyloxyiminium intermediates. Asymmetric synthesis of diastereomeric α-substituted β-amino acids

Chemistry Letters

Volumn , Issue 8, 1999, Pages 795-796

  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: 0033471716     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.795     Document Type: Article

References (21)

1. "Enantioselective Synthesis of β-Amino Acids," ed by E. Juaristi, Wiley-VCH, New York (1996).
2. a) C. N. C, Drey, in "Chemistry and Biochemistry of the Amino Acids," ed by G. C. Barrett, Chapman and Hall, London (1985), p 25.
3. b) O. W. Griffith, Ann. Rev. Biochem., 55, 855 (1986).
4. D. Seebach and J. L. Matthews, Chem. Commun., 1997, 2015.
5. A. H. Berks, Tetrahedron, 52, 331 (1996).
6. Recent reports for asymmetric synthesis of nitrogen-containing biological active compounds utilizing diastereoselective addition of nucleophiles to chiral nitrones: a) (+)-zileuton: A. Basha, R. Henry, M. A. McLaughlin, J. D. Ratajczyk, and S. J. Wittenberger, J. Org. Chem., 59, 6103 (1994).
7. b) (+)-lentiginosine: R. Giovannini, E. Marcantoni, and M. Petrini, J. Org. Chem., 60, 5706 (1995).
8. (+)-polyoxin J: A. Dondoni, S. Franco, F. Junquera, F. L. Merchán, P. Merino, and T. Tejero, J. Org. Chem., 62, 5497 (1997).
9. a) E. Breuer, in "The Chemistry of Amino, Nitroso and Nitro Compounds and Their Derivatives Part I," ed by S. Patai, Wiley, New York (1982), p. 459.
10. b) K. B. G. Torsell, "Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis," VCH, Weinheim (1988).
11. a) S.-I. Murahashi, H. Mitsui, T. Shiota, T. Tsuda, and S. Watanabe, J. Org. Chem., 55, 1736 (1990).
12. b) S.-I. Murahashi, T. Shiota, and Y. Imada, Org. Synth., 70, 265 (1992).
13. S.-I. Murahashi, Y. Imada, and H. Ohtake, J. Org. Chem., 59, 6170 (1994).
14. H. W. Heine, R. Zibuck, and W. J. A. VandenHeuvel, J. Am. Chem. Soc., 104, 3691 (1982) and references therein.
15. a) D. A. Evans, J. Bartroli, and T. L. Shih, J. Am. Chem. Soc., 103, 2127 (1981).
16. b) D. A. Evans. F. Urpí, T. C. Somers, J. S. Clark, and M. T. Bilodeau, J. Am. Chem. Soc., 112, 8215 (1990).
17. The relative configurations of 9a and 9b were determined to be anti and syn, respectively, by the NOE experiments of the trans-and cis-2-benzyl-4-methyl-3-phenylisoxazolidin-5-ones, which were prepared by hydrolyses of 9a and 9b followed by acid-catalyzed cyclizations
18. Asymmetric synthesis of α-methyl-β-phenylalanine derivatives: a) S. G. Davies and I. A. S. Walter, J. Chem. Soc., Perkin Trans. 1, 1994, 1129.
19. b) S. G. Davies, O. Ichihara, and I. A. S. Walter, J. Chem. Soc., Perkin Trans. 1, 1994, 1141.
20. The absolute configuration of the β-position of (-)-10a was determined to be S by converting (-)-10a to (S)-(-)-1-phenylpropylamine upon decarboxylation and subsequent deprotection. K. Harada and T. Okawara, J. Org. Chem., 38, 707 (1973).
21. K. S. Chu, G. R. Negrete, J. P. Konopelski, F. J. Lakner, N.-T. Woo, and M. M. Olmstead, J. Am. Chem. Soc., 114, 1800 (1992).