Catalytic Asymmetric Glyoxylate–Ene Reaction: A Practical Access to α-Hydroxy Esters in High Enantiomeric Purities

Journal of the American Chemical Society

Volumn 112, Issue 10, 1990, Pages 3949-3954

  Mikami, Koichi ^a   Terada, Masahiro ^a   Nakai, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0346630127     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00166a035     Document Type: Article

References (26)

1. Morrison, J. D. Asymmetric Synthesis; Academic Press: New York, 1984; Vol. 3B.
2. Bosnich, B. Asymmetric Catalysis; Martinus Nijhoff Publishers: Dordrecht, 1986.
3. Kagan, H. B. in Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon: New York, 1982; Vol. 8.
4. Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405.
5. Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimorl, J. J Am. Chem. Soc. 1989, 111, 5340 and references cited therein.
6. Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310.
7. Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493.
8. Omura, S. J. Synth. Org. Chem. Jpn. 1986, 44, 127.
9. Hanessian, S. Total Synthesis of Natural Products. The Chiron Approach; Pergamon: New York, 1983; Chapter 2.
10. Mori, K. in The Total Synthesis of Natural Products; Apsimon, J., Ed.; Wiley Interscience: New York, 1981; Chapter 1.
11. Seebach, D.; Hungerbuhler, E. In Modern Synthetic Methods; Scheffold, R., Ed.; Otto Salle Verlag: Frankfurt am Mein, Germany, 1980.
12. Snider, B. B. Acc. Chem. Res. 1980,13, 426.
13. Hoffmann, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 556.
14. Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476.
15. Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984.
16. Whitesell, J. K. Acc. Chem. Res. 1985, 18, 280
17. Maruoka, K.; Hoshino, Y.; Shirasaka, S.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 3967.
18. Narasaka, K.; Hayashi, Y.; Shimada, S. Chem. Lett. 1988, 1609.
19. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940
20. Mikami, K.; Terada, M.; Nakai, T. Chem. Express 1989, 4, 589.
21. Reetz, M. T.; Kyung, S.-H.; Bolm, C.; Zierke, T. Chem. Ind. 1986, 824.
22. Mikami, K.; Kasuga, T.; Fujimoto, K.; Nakai, T. Tetrahedron Lett. 1986, 27, 4185.
23. Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922.
24. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987,109, 5765. Also see refs 3a and 7a.
25. Iwasawa, N.; Hayashi, Y.; Sakurai, H.; Narasaka, K. Chem. Lett. 1989, 1581.
26. Bear, E. Fischer, J. J. Am. Chem. Soc. 1939, 61, 761.