Highly efficient synthesis of α,β-acetylenic aldehydes from terminal alkynes using DMF as the formylating reagent

Tetrahedron Letters

Volumn 39, Issue 36, 1998, Pages 6427-6428

  Journet, Michel ^a   Cai, Dongwei ^a   DiMichele, Lisa M ^a   Larsen, Robert D ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; ALDEHYDE DERIVATIVE; ALKYNE; BUFFER; LITHIUM ACETYLIDE; LITHIUM DERIVATIVE; N,N DIMETHYLFORMAMIDE; PHOSPHATE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032171542     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01352-5     Document Type: Article

References (16)

1. (1) Covarrubias-Zúñiga, A.; Rios-Barrios, E. J. Org. Chem. 1997, 62, 5688.
2. (2) a) Corey, E. J.; Lee, T. W. Tetrahedron Lett. 1997, 38, 5755.
3. b) Ishihara, K.; Kondo, S.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1997, 62, 3026.
4. (3) a) Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616.
5. b) Marshall, J. A.; Andersen, M. W. J. Org. Chem. 1992, 57, 2766.
6. (4) a) Mikami, K.; Matsueda, H.; Nakai, T. Synlett 1993, 23.
7. b) Petassis, N. A.; Teets, K. A. Tetrahedron Lett. 1993, 34, 805.
8. c) Rucker, M.; Bruckner, R. Tetrahedron Lett. 1997, 38, 7353.
9. (5) Mikami, K.; Matsueda, H.; Nakai, T. Tetrahedron Lett. 1993, 34, 3571.
10. (6) Jones, E. R. H.; Skattebøl, L.; Whiting, M. C. J. Chem. Soc. 1958, 1054.
11. (7) a) For instance, using N-formylmorpholine, 3-phenylpropynal was synthesized from lithium phenyl acetylide in 80% yield: Olah, G. A.; Ohannesian, L.; Arvanaghi, M. J. Org. Chem. 1984, 49, 3856.
12. b) Olah, G. A.; Arvanaghi, M. Angew. Chem., Int. Ed. Engl. 1981, 20, 878.
13. c) Comins, D.; Meyers, A. I. Synthesis 1978, 403.
14. d) Amaratunga, W.; Fréchet, J. M. J. Tetrahedron Lett. 1983, 24, 1143.
15. (8) All Michael adducts have a strong absorption at 325 nm.
16. (9) n-Butyllithium was titrated with N-pivaloyl-o-toluidine: Suffert, J. J. Org. Chem. 1989, 54, 509.