Mild and Efficient Synthesis of (Z)-α-Chloroalkylidene-β- lactones via the PdCl2-Catalyzed Cyclocarbonylation of 2-Alkynols

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4429-4432

  Ma, Shengming ^a   Wu, Bin ^a   Zhao, Shimin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CHLORIDE; LACTONE DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; SYNTHESIS;

EID: 0344927867     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0357245     Document Type: Article

References (40)

1. (a) Schubert, T.; Hummel, W.; Müller, M. Angew. Chem., Int. Ed. 2002, 41, 634.
2. (b) Tan, L.; Chen, C.; Tillyer, R. D.; Grabowski, E. J. J.; Reider, P. J. Angew. Chem., Int. Ed. 1999, 38, 711.
3. (c) Cassel, J. A.; Leue, S.; Gachkova, N. I.; Kann, N. C. J. Org. Chem. 2002, 67, 9460.
4. (a) López, F.; Castedo, L.; Mascareñas, J. L. J. Am. Chem. Soc. 2002, 124, 4218.
5. (b) Burova, S. A.; McDonald, F. E. J. Am. Chem. Soc. 2002, 124, 8188.
6. (c) Blandino, M.; McNelis, E. Org. Lett. 2002, 4, 3387.
7. (d) McDonald, F. E.; Wu, M. Org. Lett. 2002, 4, 3979.
8. (e) Grotjahn, D. B.; Van, S.; Combs, D.; Lev, D. A.; Schneider, C.; Rideout, M.; Meyer, C.; Hernandez, G.; Mejorado, L. J. Org. Chem. 2002, 67, 9200.
9. Rosenthal, R. W.; Schwartzman, L. H.; Greco, N. P.; Proper, R. J. Org. Chem. 1963, 28, 2835.
10. Nogi, T.; Tsuji, J. Tetrahedron 1969, 25, 4099.
11. Van den Hoven, B. G.; Ali, B. E.; Alper, H. J. Org. Chem. 2000, 65, 4131.
12. Fukuta, Y.; Matsuda, I.; Itoh, K. Tetrahedron Lett. 2001, 42, 1301.
13. Larock, R. C.; Riefling, B.; Fellows, C. A. J. Org. Chem. 1978, 43, 131.
14. Buchwald, S. L.; Fang, Q.; King, S. M. Tetrahedron Lett. 1988, 29, 3445.
15. Consorti, C. S.; Ebeling, G.; Dupont, J. Tetrahedron Lett. 2002, 43, 753.
16. Gabriele, B.; Salerno, G.; De Pascali, F.; Costa, M.; Chiusoli, G. P. J. Chem. Soc., Perkin Trans. 1 1997, 147.
17. Matsuda, I.; Ogiso, A.; Sato, S. J. Am. Chem. Soc. 1990, 112, 6120.
18. (a) Bohlmann, F.; Zdero, C.; King, R. M.; Robinson, H. Phytochemistry 1981, 20, 1069.
19. (b) Bohlmann, F.; Zdero, C.; King, R. M.; Robinson, H. Phytochemistry 1983, 22, 2860.
20. (c) Bohlmann, F.; Paul, A. H. K. Tetrahedron Lett. 1984, 25, 1697.
21. (a) Adam, W.; Albert, R.; Hasemann, L.; Nava Salgado, V. O.; Nestler, B. ; Peters, E.-M.; Peters, K.; Prechtl, F.; von Schnering, H. G. J. Org. Chem. 1991, 56, 5782.
22. (b) Danheiser, R. L.; Choi, Y. M.; Menichincheri, M.; Stoner, E. J. J. Org. Chem. 1993, 58, 322.
23. (c) Martinez, I.; Andrews, A. E.; Emch, J. D.; Ndakala, A. J.; Wang, J.; Howell, A. R. Org. Lett. 2003, 5, 399.
24. (d) For a review, see: Pommier, A.; Pons, J.-M. Synthesis 1993, 441.
25. (a) Adam, W.; Nava Salgado, V. O.; Peters, E.-M.; Peters, K.; von Schnering, H. G. Chem. Ber. 1993, 126, 1481.
26. (b) Payne, G. B. J. Org. Chem. 1966, 31, 718.
27. (c) Baxter, G. J.; Brown, R. F. C.; Eastwood, F. W.; Gatehouse, B. M.; Nesbit, M. C. Aust. J. Chem. 1978, 31, 1757.
28. (d) Ben Cheikh, A.; Pommelet, J.-C.; Chuche, J. J. Chem. Soc., Chem. Commun. 1990, 615.
29. (e) Masters, A. P.; Sorensen, T. S. Tetrahedron Lett. 1989, 30, 5869.
30. (a) Zhang, C.; Lu, X. Synthesis 1996, 586.
31. (b) Bartels, A.; Jones, P. G.; Liebscher, J. Synthesis 1998, 1645.
32. (a) Adam, W.; Albert, R.; Dachs Grau, N.; Hasemann, L.; Nestler, B.; Peters, E.-M.; Peters, K.; Prechtl, F.; von Schnering, H. G. J. Org. Chem. 1991, 56, 5778.
33. (b) Adam, W.; Hasemann, L.; Prechtl, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 1536.
34. int = 0.0761), no observation [I > 2σ(I)] 2497, parameters 393.
35. int = 0.1504), no observation [I > 2σ(I)] 1514, parameters 212.
36. (a) For a recent review on the synthesis of optically active propargylic alcohols, see: Ma, S.; He, Q. Chin. J. Org. Chem. 2002, 6, 375.
37. (b) Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806.
38. (a) Ma, S.; Lu, X. J. Org. Chem. 1993, 58, 1245.
39. (b) Li, J.; Jiang, H.; Feng, A.; Jia, L. J. Org. Chem. 1999, 64, 5984.
40. (c) Huang, X.; Sun, A. J. Org. Chem. 2000, 65, 6561.