Synthesis of N-heterocycles via lactam-derived ketene aminal phosphates. Asymmetric synthesis of cyclic amino acids

Chemical Communications

Volumn , Issue 16, 1998, Pages 1757-1758

  Nicolaou, K C ^a   Shi, Guo Qiang ^a   Namoto, Kenji ^a   Bernal, Federico ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000436139     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a804198i     Document Type: Article

References (12)

1. For the use of lactam-derived enol triflates in carbon-carbon bond forming reactions, see: T. Okita and M. Isobe, Synlett, 1994, 589;
2. T. Okita, and M. Isobe, Tetrahedron, 1995, 51, 3737;
3. T. Luker, H. Hiemstra and W. N. Speckamp, Tetrahedron Lett., 1996, 37, 8257;
4. T. Luker, H. Hiemstra and W. N. Speckamp, J. Org. Chem., 1997, 62, 3592;
5. T. Luker, H. Hiemstra and W. N. Speckamp, J. Org. Chem., 1997, 62, 8131.
6. For the use of lactone-derived ketene acetal phosphates, see: K. C. Nicolaou, G.-Q. Shi, J. L. Gunzner, P. Gärtner and Z. Yang, J. Am. Chem. Soc., 1997, 119, 5467.
7. The larger lactams were synthesized from the corresponding ketones via a Beckmann rearrangement, see: G. A. Olah and A. P. Fung, Synthesis, 1979, 537.
8. W. J. Scott and J. K. Stille, J. Am. Chem. Soc., 1986, 108, 3033.
9. BINAP has been previously used as a superior ligand to monodentate and other bidentate systems in aromatic animation; see: J. P. Wolfe, S. Wagaw and S. L. Buchwald, J. Am. Chem. Soc., 1996, 118, 7215.
10. For a catalytic hydrogenation review, see: R. Noyori, Asymmetric Catalysis In Organic Synthesis, Wiley-Interscience, New York, 1994, ch. 2.
11. To the best of our knowledge, there is only one example of a catalytic asymmetric hydrogenation of a cyclic dehydroamino acid derivative, see: C. J. Foti and D. L. Comins J. Org. Chem., 1995, 60, 2656.
12. M. J. Burk, M. F. Gross, T. Gregory, P. Harper, C. S. Kalberg, J. R. Lee and J. P. Martinez, Pure Appl. Chem., 1996, 68, 37.