Formation of homoallyl stannanes via palladium-catalyzed stannylative cyclization of enynes

Organic Letters

Volumn 2, Issue 5, 2000, Pages 671-673

  Lautens, Mark ^a   Mancuso, John ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001084236     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005508l     Document Type: Article

References (18)

1. General review on use of organostannanes in synthesis: Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths: London, 1987.
2. (a) Corey, E. J.; Wollenberg, R. H. J. Org. Chem, 1975, 40, 2265.
3. (b) Corey, E. J.; Wollenberg, R. H. J. Am. Chem. Soc. 1974, 96, 5581.
4. (a) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction: John Wiley & Sons: New York, 1998.
5. (b) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
6. (c) Milstein, D.; Stille, J. K. J. Am. Chem. Soc: 1978, 100, 3636.
7. (a) Plamondon, L.; Wuest, J. D. J. Org. Chem. 1991, 56, 2066-2075.
8. (b) Sato, T. Synthesis 1990, 259-270.
9. Leading references: (a) Betzer, J.-F.; Delaloge, F.; Muller, B. Pancrazi, A.; Prunet, J. J. Org. Chem. 1997, 77688.
10. (b) Gevorgyan, V. Liu, J. X.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2963.
11. (c) Lautens, M. Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676-10677.
12. (d) Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857.
13. Lautens, M.; Smith, N. D.; Ostrovsky, D. J. Org. Chem. 1997, 62, 8970.
14. Widenhoefer, R. A.; DeCarli, M. A. J. Am. Chem. Soc. 1998, 120, 3805-3806.
15. 2 was not effective as a catalyst for this reaction, giving only 3% cyclized product.
16. Onozawa, S.-Y.; Hatanaka, Y.; Choi, N.; Tanaka, M. Organometallics 1997, 16, 5389-5391.
17. (a) Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867.
18. (b) Miyake, H.; Yamamura, K. Chem. Lett. 1988, 981-984.