Stereoselective synthesis of hex-2-(E)-en-4-yn-1,6-dioates and E,Z-muconic acid diesters via organo-catalyzed self-coupling of propiolates

Tetrahedron Letters

Volumn 46, Issue 15, 2005, Pages 2547-2549

  Ramachandran, P Veeraraghavan ^a   Rudd, Michael T ^a   Reddy, M Venkat Ram ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

DABCO; E,Z Dienes; Enynes; Muconic acid esters; Self coupling

Indexed keywords

1,4 DIAZABICYCLO[2.2.2]OCTANE; ESTER DERIVATIVE; MUCONIC ACID; VERRUCARIN A;

ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; HYDROGENATION; POLYMERIZATION; QUANTITATIVE ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 15244341085     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.098     Document Type: Article

References (18)

1. P.V. Ramachandran, M.V.R. Reddy, and M.T. Rudd Tetrahedron Lett. 40 1999 3819
2. C. Tamm, and N. Jeker Tetrahedron 45 1989 2385 and references cited therein
3. Pollart, K. A. U.S. Patent 3,383,403. Chem. Abstr. 1968, 69, P35475k
4. Tsuji, J.; Imamura, S. Japan 68 00,489. Chem. Abstr. 1968, 69, P35463e
5. W.C. Still, and H.J. Ohmizu J. Org. Chem. 46 1981 5242
6. P. Mohr, M. Tori, P. Grossen, P. Herold, and C. Tamm Helv. Chim. Acta 65 1982 1412
7. B.M. Trost, and P.G. McDougal J. Org. Chem. 49 1984 458
8. W.R. Roush, and T.A. Blizzard J. Org. Chem. 45 1984 2385
9. R.A. Aitken, J.I.G. Cadogan, and I. Gosney J. Chem. Soc., Perkin Trans. 1 1994 1983
10. X. Lu, X. Huang, and S. Ma Tetrahedron Lett. 33 1992 2535
11. A.B. McKague Synth. Commun. 29 1999 1463
12. E. Vogel Liebigs Ann. Chem. 615 1958 14
13. P.C. Guha, and D.K. Sankaran Org. Synth. 26 1946 57
14. E. Wenkert, K.A.H. Adams, and C.L. Leicht Can. J. Chem. 41 1963 1844
15. No mention of the stereochemistry of the double bond is made in the patent
16. M.-E. Martin, D. Planchenault, and F. Huet Tetrahedron 51 1995 4985
17. J.H. Rigby, H.S. Ateeq, N.R. Charles, S.V. Cuisiat, M.D. Ferguson, J.A. Henshilwood, C. Krueger, C.O. Ogbu, K.M. Short, and M.J. Heeg J. Am. Chem. Soc. 115 1993 1382
18. M. Jones Jr., and R.H. Levin J. Am. Chem. Soc. 91 1969 6411