Catalytic Asymmetric Arylation of 2,3-Dihydrofuran with Aryl Triflates

Journal of the American Chemical Society

Volumn 113, Issue 4, 1991, Pages 1417-1419

  Ozawa, Fumiyuki ^a   Kubo, Akihiko ^a   Hayashi, Tamio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85022586647     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00004a056     Document Type: Article

References (34)

1. Torii, S.; Okumoto, H.; Akahoshi, F.; Kotani, T. J. Am. Chem. Soc. 1989, 111, 8932.
2. Larock, R. C.; Fried, C. A. J. Am. Chem. Soc. 1990, 112, 5882.
3. Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407.
4. Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603.
5. Larock, R. C.; Baker, B. E. Tetrahedron Lett. 1988, 29, 905.
6. Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919.
7. Zhang, Y.; Negishi, E. J. Am. Chem. Soc. 1989, 111, 3454.
8. Zhang, Y.; O'Connor, B.; Negishi, E. J. Org. Chem. 1988, 53, 5588.
9. Negishi, E.; Zhang, Y.; O'Connor, B. Tetrahedron Lett. 1988, 29, 2915.
10. Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464.
11. Mori, M.; Kubo, Y.; Ban, Y. Tetrahedron 1988, 44, 4321.
12. Grigg, R.; Stevenson, P.; Worakun, T. Tetrahedron 1988, 44, 2049.
13. Daves, G. D., Jr.; Hallberg, A. Chem. Rev. 1989, 89, 1433.
14. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738.
15. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5846.
16. Shibasaki has found very recently that an optically active cis-decalin derivative of 80% ee is formed by the intramolecular Heck reaction of an alkenyl iodide catalyzed by Pd(OAc)2-(R)-BINAP complex in the presence of silver phosphate: Sato, Y.; Sodeoka, M.; Shibasaki, M. Chem. Lett. 1990, 1954.
17. (R)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl: Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629 and references cited therein.
18. Yamamoto, A. Organotransition Metal Chemistry; Wiley: New York; 1986; p 383.
19. Brumbaugh, J. S.; Whittle, R. R.; Parvez, M.; Sen, A. Organometallics 1990, 9, 1735.
20. Samsel, E. G.; Norton, J. R. J. Am. Chem. Soc. 1984, 106, 5505.
21. Examples of Heck-type reactions using organic triflates: ref 2b. Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1990, 55, 3654.
22. Andersson, C. M.; Hallberg, A. J. Org. Chem. 1989, 54, 1502; 1988, 53, 2112. Friess, B.; Cazes, B.; Gore, J. Tetrahedron Lett. 1988, 29, 4089.
23. Andersson, C. M.; Hallberg, A. J. Org. Chem. 1988, 53, 2112.
24. Friess, B.; Cazes, B.; Gore, J. Tetrahedron Lett. 1988, 29, 4089.
25. Cacchi, S.; Ciattini, P. G.; Morera, E.; Ortar, G. Tetrahedron Lett. 1987, 28, 3039.
26. Hirota, K.; Kitade, Y.; Isobe, Y.; Maki, Y. Heterocycles 1987, 26, 355.
27. Scott, W. J.; Pena, M. R.; Sward, K.; Stoessel, S. J.; Stille, J. K. J. Org. Chem. 1985, 50, 2302.
28. Preparation of racemic compounds of 2a, 3a, 2b, 3f, and 2g has been reported. 2a: Scribe, P.; Wiemann, J. Bull. Soc. Chim. Fr. 1971, 2268.
29. 3a: ref 1d. 2b: Dana, G.; Touboul, E.; Convert, O. Tetrahedron Lett. 1989, 45, 3371.
30. 3f: Lee, T. D.; Daves, G. D., Jr. J. Org. Chem. 1983, 45, 399.
31. 2g: ref 1c.
32. The enantiomeric purities of 2 and 3 were determined by 1H NMR analysis with optically active NMR shift reagent Eu(hfc)3. The absolute configuration of (−)-2a (84% ee) was determined by converting it with Jones reagent into known γ-butyrolactone derivative, (R)-(+)-3-phenyl-2-oxa-cyclopentanone (9a, 84% optical purity, [α]20D +27.4° (c 1.1, CHCl3)).10 The absolute configuration of (−)-3a was determined as follows. Hydrogenation of (R)-(−)-2a (93% ee) with Wilkinson catalyst in benzene at room temperature under an atmospheric pressure of dihydrogen gave (R)-(+)-2-phenyl-tetrahydrofuran (10a, [α]20D +45.0° (c 1.1, CHCl3)), while hydrogenation of (−)-3a (59% ee) under similar conditions gave (S)-(−)-10a ([α]20D−17.0° (c 0.92, CHCl3)). The absolute configurations of 2b-g and 3b-f were assigned by similarity in shifts using the chiral shift reagent.
33. (S)-(−)-9a ([α]D −32.5° (c 4.3, CHCl3)): Manzocchi, A.; Casati, R.; Fiecchi, A.; Santaniello, E. J. Chem. Soc., Perkin Trans. 1 1987, 2753.
34. Optical purities of (R)-1a formed in the reactions of phenyl triflate (0.64 mmol), 2,3-dihydrofuran (3.2 mmol), and Et3N (1.9 mmol) in various solvents (2 mL) in the presence of 3 mol % of Pd(OAc)2-(R)-BINAP catalyst at 40 °C are as follows: benzene (71% ee), THF (67% ee), CH2C12 (57% ee), and DMF (63% ee).