Stereoselective Synthesis of α-(Chloromethylene)-γ-butyrolactone Derivatives from Acyclic Allylic 2-Alkynoates

Journal of Organic Chemistry

Volumn 58, Issue 5, 1993, Pages 1245-1250

  Ma, Shengming ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33751385850     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00057a043     Document Type: Article

References (35)

1. Hoffmann, H. M. R.; Rube, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94.
2. Ma, S.; Lu, X. J. Chem. Soc., Chem. Commun. 1990, 773.
3. Ma, S.; Lu, X. J. Org. Chem. 1991, 56, 5120 and references cited therein.
4. Grieco, P. A. Synthesis 1975, 67.
5. Petragnani, N.; Ferraz, H. M. C.; Silva, G. V. J. Synthesis 1986, 157.
6. Larock, R. C.; Harrison, L. W.; Hsu, M. H. J. Org. Chem. 1984, 49, 3662.
7. Kobrich, G.; Flory, K. Chem. Ber. 1966, 99, 1773.
8. Minami, T.; Niki, I.; Agawa, T. J. Org. Chem. 1974, 39, 3236.
9. Tanaka, K.; Tamura, N.; Kaji, A. Chem. Lett. 1980, 595.
10. Ito, Y.; Aoyama, H.; Saegusa, T. J. Am. Chem. Soc. 1980, 102, 4519.
11. Castro, C. E.; Gaughan, E. J.; Owsley, D. C. J. Org. Chem. 1965, 30, 587.
12. Weber, W. P.; Felix, R. A.;Willard, A. K.; Koenig, K. E. Tetrahedron Lett. 1971, 4701.
13. Trost, B. M. Tetrahedron 1977, 33, 2615.
14. Hosokawa, T.; Moritani, I.; Nishioka, S. Tetrahedron Lett. 1969, 3833;
15. Chatt, J.; Vallarino, L. M.; Venanzi, L. M. J. Chem. Soc. 1957, 3413.
16. Henry, P. M. Palladium Catalyzed Oxidation of Hydrocarbons; D. Reidel: Dordrecht, Holland, 1980; p 78.
17. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds, Mechanistic Principles and Synthetic Methodology Including Biochemical Processes; Academic Press: New York, 1981; Chapter 7.
18. Budnik, R. A.; Kochi, J. K. J. Organomet. Chem. 1976, 116, C3.
19. Curran, D. P.; Chang, C.-T. Tetrahedron Lett. 1990, 31, 933.
20. Bäckvall, J.-E.; Akermark, B.; Ljunggren, S. O. J. Chem. Soc., Chem. Commun. 1977, 264.
21. Bäckvall, J.-E. Tetrahedron Lett. 1977, 467.
22. Nagashima, H.; Seki, K.; Ozaki, N.; Wakamatsu, H.; Itoh, K.; Tamo, Y.; Tsuji, J. J. Org. Chem. 1990, 55, 985.
23. Heck, R. F. Pure Appl. Chem. 1978, 50, 691.
24. Antonsson, T.; Moberg, C.; Tottie, L.; Henmann, A. J. Org. Chem. 1989, 54, 4914.
25. Yamamoto, A. Organotransition Metal Chemistry; John Wiley: New York, 1986; p 223.
26. Huttel, R.; Kratzer, J. Angew. Chem. 1959, 71, 456.
27. Huttel, R.; Kratzer, J.; Bechter, M. Chem. Ber. 1961, 94, 766.
28. Doyle, J. R.; Slade, P. E.; Jonaasen, H. B. Inorg. Synth. 1960, 6, 218.
29. Ukai, T.; Kawazura, H.; Ishii, Y. J. Organomet. Chem. 1974, 65, 253.
30. Simmross, F.-M.; Weyerstahl, P. Synthesis 1981, 72.
31. Heilbron, I.; Jones, E. R. H.; Sondheimer, F. J. Chem. Soc. 1949, 604.
32. Ma, S.; Lu, X.; Li, Z. J. Org. Chem. 1992, 57, 709.
33. Bahurel, Y.; Collonges, F.; Menet, A.; Pautet, F.; Poncet, A.; Descotes, G. Bull. Soc. Chim. Fr. 1971, 2203.
34. Miller, L. A. U.S. 3,210,405, 1965;
35. Chem. Abstr. 1965, 63, P17971h.