Palladium-catalyzed enantioselective carbonylative cyclization of aryl and alkenyl triflates with carbon monoxide

Organic Letters

Volumn 1, Issue 9, 1999, Pages 1487-1489

  Hayashi, Tamio ^a   Tang, Jun ^a   Kato, Kazuhiko ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000458519     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9902879     Document Type: Article

References (23)

1. For a review, see: Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds; Plenum: New York 1991
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3. (b) Tour, J. M.; Negishi, E. J. Am. Chem. Soc. 1985, 107, 8289.
4. (c) Negishi, E.; Copéret, C.; Ma, S.; Mita, T.; Sugihara, T.; Tour, J. M. J. Am. Chem. Soc. 1996, 118, 5904.
5. (d) Negishi, E.; Ma, S.; Amanfu, J.; Copéret, C.; Miller, J. A.; Tour, J. M. J. Am. Chem. Soc. 1996, 118, 5919.
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8. (g) Torii, S.; Okumoto, H.; Xu, L.-H. Tetrahedron Lett. 1990, 31, 7175.
9. (h) Grigg, R.; Pratt, R. Tetrahedron Lett. 1997, 38, 4489.
10. Asymmetric catalytic cyclocarbonylation via a hydrido-palladium intermediate: (a) Yu, W.-Y.; Bensimon, C.; Alper, H. Chem. Eur. J. 1997, 3, 417.
11. (b) Okuro, K.; Kai, H.; Alper, H. Tetrahedron: Asymmetry 1997, 8, 2307.
12. Consiglio, G. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993.
13. For details, see the following. Hydroformylation: (a) Sakai, N.; Mano, S.; Nozaki, K.; Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033.
14. (b) Sperrle, M.; Consiglio, G. J. Am. Chem. Soc. 1995, 117, 12130.
15. Alternating carbonylative copolymerization: (c) Nozaki, K.; Sato, N. Takaya, H. J. Am. Chem. Soc. 1995, 117, 9911.
16. Tada, Y.; Satake, A.; Shimizu, I.; Yamamoto, A. Annual Meeting of the Chemical Society of Japan, 1997, 4 F1 40.
17. Takaya, H.; Mashima, S.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
18. The carbonylative cyclization was slower at temperatures lower than 80°C, and the higher temperature resulted in some loss of enantioselectivity.
19. 3 resulted in obvious loss of enantioselectivity.
20. When the ratio of Ligand/Pd is less than 2, palladium black precipitates, resulting in a low conversion of triflate.
21. This reaction is inhibited by high CO pressure.
22. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
23. For alkenyl triflates, the (S)-binap/dioxane system gave a considerable amount of 6-endo cyclization product. With the (S)-tol-binap/benzene system, the 6-endo cyclization was retarded to some extent, and the enantioselectivity was obviously improved.