Heterocycles in asymmetric synthesis. Part 1. construction of the chiral building blocks for enantioselective alkaloid synthesis via an asymmetric intramolecular michael reaction

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 4, 1992, Pages 509-516

  Hirai, Yoshiro ^a   Terada, Takashi ^a   Yamazaki, Takao ^a   Momose, Takefumi ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343520793     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19920000509     Document Type: Article

References (26)

1. A. Alexakis, M. J. Chapdelaine and G. H. Posner, Tetrahedron Lett., 1978, 4209
2. G. Stork, C. S. Shiner and J. D. Winkler, J. Am. Chem. Soc, 1982, 104, 310
3. Y. Hirai, A. Hagiwara and T. Tamazaki, Heterocycles, 1986, 24, 571
4. P. Rosenmund and M. H. Merescht, Tetrahedron Lett., 1990, 31, 647.
5. Leading recent references to asymmetric intermolecular Michael reactions: W. Oppolzer, P. Dudfield, T. Stevenson and T. Godel, Hetv. Chim. Acta, 1985, 68, 212
6. C. Stetin, B. D. Jeso and J.-C. Pommier, J. Org. Chem., 1985, 50, 3863
7. M. Pfau, G. Revial, A. Guingant and J. Angelo, J. Am. Chem. Soc, 1985, 107, 273
8. D. Enders, K. Papadopoulos, B. E. M. Rendenbach, R. Appel and F. Knoch, Tetrahedron Lett., 1986, 27, 3491
9. K. Fuji, M. Node, H. Nagasawa, Y. Naniwa and S. Terada, J. Am. Chem. Soc, 1986,108, 3855
10. K. Tomioka, K. Ando, K. Yasuda and K. Koga, Tetrahedron Lett., 1986, 27, 715
11. G. H. Posner and C. Switzer, J. Am. Chem. Soc, 1986, 108, 1239
12. K. Tomioka, W. Seo, K. Ando and K. Koga, Tetrahedron Lett., 1987, 28, 6637
13. S. Aoki, S. Sasaki and K. Koga, Tetrahedron Lett., 1989, 30, 7229.
14. The only example leading, however, to one enantiomeric counterpart is the one reported by B. M. Trost, C. D. Shuey, F. D. Ninno and S. S. McElvain Jr., J. Am. Chem. Soc, 1979, 101, 1284.
15. G. Stork and N. A. Saccomano, Tetrahedron Lett., 1987, 28, 2087.
16. G. Stork, A. Brizzolara, H. Landesman, J. Szmuszkovicz and R. Terrell, J. Am. Chem. Soc, 1963, 85, 207.
17. H. V. Meyers, J. Am. Chem. Soc, 1988, 110, 5198
18. J. Angelo, G. Revial, T. Volpe and M. Pfau, Tetrahedron Lett., 1988, 29, 4427 and references cited therein.
19. Y. Hirai, T. Terada and T. Yamazaki, J. Am. Chem. Soc, 1988,110,958.
20. Y. Hirai, I. Kamide and T. Yamazaki, Heterocycles, 1981, 15, 1101.
21. Y. Hirai, T. Terada, A. Hagiwara and T. Yamazaki, Chem. Pharm. Bull., 1988,36, 1343.
22. S. Takano, S. Satoh, K. Ogasawara and K. Aoe, Heterocycles, 1990, 30, 583.
23. R. D. Allan, Tetrahedron Lett., 1978, 2199.
24. J. A. Dale, D. L. Dull and H. S. Mosher, J. Org. Chem., 1969,34,2543.
25. A. Sevin, J. Tortajada and M. Pfau, J. Org. Chem., 1986, 51, 2671
26. D. Seebach and J. Golinski, Helv. Chim. Acta, 1981, 64, 1413.