Sequential cross-metathesis/phosphorus-based olefination: stereoselective synthesis of 2,4-dienoates

Tetrahedron Letters

Volumn 48, Issue 31, 2007, Pages 5367-5370

  Paul, Tapas ^a   Andrade, Rodrigo B ^a  

^a Temple University   (United States)

Author keywords

2,4 Dienoates; Cross metathesis; Olefination; One pot; Tandem

Indexed keywords

ALKENE DERIVATIVE; PHOSPHORUS; REAGENT;

ARTICLE; HORNER REACTION; HORNER WADSWORTH EMMONS REACTION; OLEFINATION; ORGANIC CHEMISTRY; STEREOCHEMISTRY; SYNTHESIS;

EID: 34347401667     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.031     Document Type: Article

References (22)

1. Ho T.-L. Tandem Organic Reactions (1992), Wiley, New York
2. For CM reviews see:. Connon S.J., and Blechert S. Angew. Chem., Int. Ed. 42 (2003) 1900 and references cited therein
3. Chatterjee A.K., Choi T.-L., Sanders D.P., and Grubbs R.H. J. Am. Chem. Soc. 125 (2003) 11360
4. Scholl M., Ding S., Lee C.W., and Grubbs R.H. Org. Lett. 1 (1999) 953
5. Maryanoff B.E., and Reitz A.B. Chem. Rev. 89 (1989) 863
6. Wadsworth Jr. W.S. Org. React. 25 (1977) 73
7. See Ref. 5.
8. van den Tempel P.J., and Huisman H.O. Tetrahedron 22 (1966) 293
9. Sato K., Mizuno S., and Hirayama M. J. Org. Chem. 32 (1967) 177
10. Funk T.W., Efskind J., and Grubbs R.H. Org. Lett. 7 (2005) 187
11. Moura-Letts G., and Curran D.P. Org. Lett. 9 (2007) 5
12. Andrade R.B., and Martin S.F. Org. Lett. 7 (2005) 5733
13. Ferrie L., Amans D., Reymond S., Bellosta V., Capdevielle P., and Cossy J. J. Organomet. Chem. 691 (2006) 5456
14. During the review of this manuscript, Snapper published an article concerning the ruthenium-catalyzed tandem cross-metathesis/Wittig olefination of terminal olefins for the synthesis of (2E,4E)-dienoates:. Murelli R.P., and Snapper M.L. Org. Lett. 9 (2007) 1749
15. 13C NMR) were in agreement for the following known compounds: Compound 9:. Spino C., Rezaei H., Dupont-Gaudet K., and Belanger F. J. Am. Chem. Soc. 126 (2004) 9926
16. Compound 10:. Xuan J.X., and Fry A.J. Tetrahedron Lett. 42 (2001) 3275
17. Compound 11:. Montserrat C., de March P., Figueredo M., Font J., and Soria A. Tetrahedron 53 (1997) 16803
18. Compound 12:. Horsham M.A., Class T.J., Johnston J.J., and Casida J.E.J. Agric. Food Chem. 37 (1989) 777
19. +, 227.1283; found, 227.1277
20. Still W.C., and Gennari C. Tetrahedron Lett. 24 (1983) 4405
21. Attempts at transferring a solution of crude enal in dichloromethane from the CM step to an ethereal solution of the appropriate phosphonate anion resulted in lower product yields.
22. +, 299.2043; found, 299.2056