Palladium-Catalyzed Tandem Cyclization of Allenyl-Aldehydes and -Ketones with Aryl Iodides and Bu3SnSnBu3

Organic Letters

Volumn 4, Issue 7, 2002, Pages 1143-1144

  Ha, Young Hwan ^a   Kang, Suk Ku ^a  

^a Sungkyunkwan University   (South Korea)

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EID: 0000771905     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025557t     Document Type: Article

References (18)

1. (a) Trost, B. M. Science 1991, 254, 1471-1477.
2. (b) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281.
3. (c) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16.
4. (a) Hall, N. Science 1994, 266, 32-34.
5. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
6. Jeong, N.; Seo, S. D.; Shin, J. Y. J. Am. Chem. Soc. 2000, 122, 10220-10221.
7. Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609-4610.
8. Yamasaki, S.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 1256-1257.
9. Kang, S.-K.; Ha, Y.-H.; Ko, B.-S.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2001, 41, 343-345.
10. Yang, F.-Y.; Wu, M.-Y.; Cheng, C.-H. Tetrahedron Lett. 1999, 40, 6055-6058.
11. Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 6641-6647.
12. The condensation of allylic stannanes and aldehydes catalyzed by known palladium and platinum complexes is primarily limited to simple allylic stannanes and crotyl stannanes. See: (a) Nakamura, H.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 122, 11529-11530.
13. (b) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 1459-1460.
14. The intermolecular allylation of allenes with aldehydes via palladium-catalyzed hydrostannylation has been reported: Cheng, H.-M.; Cheng, C.-H. Org. Lett. 2000, 2, 3439-3442.
15. Carbonyl allylation of allylic derivatives by charge-reversal of electrophilic π-allylpalladium intermediates: (a) Masuyama, Y.; Hayashi, R.; Otake, K.; Kurusu, Y. J. Chem. Soc., Chem. Commun. 1988, 44-45.
16. (b) Masuyama, Y.; Otake, K.; Kurusu, Y. Tetrahedron Lett. 1988, 29, 3563-3566.
17. (c) Takahara, J. P.; Masuyama, Y.; Kurusu, Y. J. Am. Chem. Soc. 1992, 114, 2577-2586.
18. 3 (5 mol %) in THF (3 mL) was added bis(tributyltin) (244 mg, 0.42 mmol). The reaction mixture was stirred at room temperature for 12 h, and THF was evaporated in vacuo. The crude product was separated by column chromatography (hexane/ethyl acetate = 2:1) to give the cyclized products cis-3a (85 mg, 65%) and trans-3a (17 mg, 13%).