Preparation and Palladium Mediated Cross-Coupling Reactions of cis-2,3-Disubstituted 5-Halo Dihydropyran-4-ones

Synlett

Volumn 1997, Issue 8, 1997, Pages 968-970

  Evans, P Andrew ^a   Nelson, Jade D ^a   Manangan, Thara ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002701426     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-958     Document Type: Article

References (23)

1. (a) Smith, A. B., III; Branca, S. J.; Guaciaro, M. A.; Wovkulich, P. M.; Korn, A. Organic Syntheses; Freeman, J. P., Ed.; John Wiley and Sons: New York, 1983, Collect. Vol. 7, p 271.
2. (b) Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917.
3. (c) Dieter, R. K.; Nice, L. E.; Velu, S. E. Tetrahedron Lett. 1996, 37, 2377 and pertinent references cited therein.
4. (a) Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 919.
5. (b) Newhouse, B. J.; Meyers, A. I.; Sirisoma, N. S.; Braun, M. P.; Johnson, C. R. Synlett 1993, 573.
6. (c) Hodgson, D. M.; Witherington, J.; Moloney, B. A.; Richards, I. C.; Brayer, J. Synlett 1994, 32.
7. (d) Comins, D. L.; Joseph, S. P.; Chen, X. Tetrahedron Lett. 1995, 36, 9141.
8. (e) Rossi, R.; Bellina, F.; Carpita, A. Synlett 1996, 356 and pertinent references cited therein.
9. (a) Postema, M. H. D. Tetrahedron, 1992, 48, 8545.
10. (b) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683.
11. (c) Alvarez, E.; Candenas, M. -L.; Perez, R.; Ravelo, J. L.; Martin, J. D. Chem. Rev. 1995, 95, 1953 and pertinent references cited therein.
12. Evans, P. A.; Brandt, T. A. Tetrahedron Lett. 1996, 37, 6443. Evans, P. A.; Brandt, T. A. J. Org. Chem. 1997, 62, in press.
13. Evans, P. A.; Brandt, T. A. Tetrahedron Lett. 1996, 37, 6443. Evans, P. A.; Brandt, T. A. J. Org. Chem. 1997, 62, in press.
14. Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123 and pertinent references cited therein.
15. For the oxidation of trimethylsilyl derivatives with iodosobenzene, see: Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406.
16. Evans, P. A.; Nelson, J. D. J. Org. Chem. 1996, 61, 7600.
17. 13C NMR) and analytical (HRMS) data in accord with the assigned structure.
18. 4), filtered and concentrated in vacuo to afford the crude product. Purification by flash chromatography on silica gel (eluting with a 5%-20% ethyl acetate/ hexanes gradient) furnished the α-bromo or α-iodo dihydropyran-4-ones 2/3 respectively.
19. Halogenation of acyclic vinylogous esters proceeds smoothly for bromination, while iodination leads to a complex reaction mixture. The vinylogous carbonate and sulfonate 8a/b were convened to the α-bromo vinylogous carbonate and sulfonate 9a/b in 90% and 93% yield respectively. (Matrix Presented)
20. (a) Stille, J. K. Angew. Chem. Int. Ed. Engl. 1986, 25, 508.
21. (b) Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359.
22. (c) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
23. 4), filtered and concentrated in vacuo to afford the crude product. Purification by flash chromatography on silica gel (eluting with a 5%-15% ethyl acetate/hexanes gradient) furnished the α-vinyl dihydropyran-4-one 5 (166 mg, 76%) as a white crystalline solid: mp 72-73°C.