Preparation and decarboxylative rearrangement of (Z)-enyne esters

Tetrahedron Letters

Volumn 48, Issue 32, 2007, Pages 5679-5682

  Woo, Jacqueline C S ^a   Walker, Shawn D ^a   Faul, Margaret M ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; ENOL TOSYLATE; ESTER DERIVATIVE; PALLADIUM; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CYCLIZATION; DECARBOXYLATION; HYDROLYSIS; ISOMERIZATION; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 34447251580     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.012     Document Type: Article

References (33)

1. Negishi E., and Anastasia L. Chem. Rev. 103 (2003) 1979-2017
2. Alonso F., Beletskaya I.P., and Yus M. Chem. Rev. 104 (2004) 3079-3159
3. Yao T., and Larock R.C. J. Org. Chem. 68 (2003) 5936-5942
4. Anastasia L., Xu C., and Negishi E. Tetrahedron Lett. 43 (2002) 5673-5676
5. Saito S., and Yamamoto Y. Chem. Rev. 100 (2000) 2901-2915
6. For a recent example see:. Furstner A., Dierkes T., Thiel O.R., and Blanda G. Chem. Eur. J. 7 (2001) 5286-5298
7. Takahashi S., Kuroyama Y., Sonogashira K., and Hagihara N. Synthesis (1980) 627
8. Piers E., Wong T., and Coish P.D. Can. J. Chem. 72 (1994) 1816-1819
9. Wu J., Liao Y., and Yang Z. J. Org. Chem. 66 (2001) 3642-3645
10. Fu X., Zhang S., Yin J., McAllister T.L., Jiang S.A., Tann C.-H., Thiruvengadam T.K., and Zhang F. Tetrahedron Lett. 43 (2002) 573-576
11. Fu X., Zhang S., Yin J., and Schumacher D.P. Tetrahedron Lett. 43 (2002) 6673-6676
12. Baxter J.M., Steinhuebel D., Palucki M., and Davies I.W. Org. Lett. 7 (2005) 215-218
13. Milne J.E., and Buchwald S.L. J. Am. Chem. Soc. 126 (2004) 13028-13032
14. To the best of our knowledge, this is the first report of a Negishi alkynylation employing tosylates. For examples of Pd-catalyzed Suzuki-Miyaura couplings of aryl- and vinyl tosylates:. Huffman M.A., and Yasuda N. Synlett (1999) 471-473
15. Lakshman M.K., Thompson P.F., Nuqui M.A., Hilmer J.H., Sevova N., and Boggess B. Org. Lett. 4 (2002) 1479-1482
16. Nguyen H.N., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 125 (2003) 11818-11819
17. For Kumada couplings:. Limmert M.E., Roy A.H., and Hartwig J.F. J. Org. Chem. 70 (2005) 9364-9370
18. For additional examples of Suzuki, Sonogashira and Stille cross-coupling reactions:. Steinhuebel D., Baxter J.M., Palucki M., and Davies I.W. J. Org. Chem. 70 (2005) 10124-10127
19. Guram A.S., King A.O., Allen J.G., Wang X., Schenkel L.B., Chan J., Bunel E.B., Faul M.M., Larsen R.D., Martinelli M.J., and Reider P.J. Org. Lett. 8 (2006) 1787-1789
20. 2] in THF (2 mL) was added and the addition flask rinsed with THF (1 mL). The resulting mixture was heated at 40 °C for 24 h, cooled, filtered and concentrated. The residue obtained was purified by flash chromatography on silica gel (ethyl acetate-hexanes) to afford the (Z)-enyne ester.
21. 4, THF, rt, 16 h] of propynylzinc bromide with iodide 4.
22. Additional base charges or extended heating times resulted in competitive retro-aldol reaction of the enone products.
23. 2O) conditions were examined.
24. General procedure for decarboxylative rearrangement: To a stirred solution of (Z)-enyne ester (1.31 mmol) in THF (1.5 mL) and MeOH (1 mL) was added aqueous KOH (1.05 mL, 2.5 N, 2.62 mmol) and the resulting mixture was heated at 80 °C for 16 h. The reaction mixture was cooled to rt, diethyl ether (20 mL), aqueous HCl (5.0 mL, 1.0 N) and water (10 mL) were added and the layers were separated. The aqueous phase was extracted with ether (20 mL) and the combined organic layers were concentrated. The residue obtained was purified by flash chromatography on silica gel (ethyl acetate-hexanes) to afford the desired enone.
25. Nakamura I., and Yamamoto Y. Chem. Rev. 104 (2004) 2127-2198
26. Harkat H., Weibel J.-M., and Pale P. Tetrahedron Lett. (2006) 6273-6276
27. Uchiyama M., Ozawa H., Takuma K., Matsumoto Y., Yonehara M., Hiroya K., and Sakamoto T. Org. Lett. 24 (2006) 5517-5520
28. Baldwin J.E. J. Chem. Soc., Chem. Commun. (1976) 734-736
29. Soliman G., and El-Kholy I. J. Chem. Soc. (1955) 2911-2913
30. Kato Y., Okada S., Tomimoto K., and Mase T. Tetrahedron Lett. (2001) 4849-4851
31. Walker S.D., Barder T.E., Martinelli J.R., and Buchwald S.L. Angew. Chem., Int. Ed. 43 (2004) 1871-1876
32. Barder T.E., Walker S.D., Martinelli J.R., and Buchwald S.L. J. Am. Chem. Soc. 127 (2005) 4685-4696
33. Billingsley K.L., Anderson K.W., and Buchwald S.L. Angew. Chem., Int. Ed. 45 (2006) 3484-3488