Nucleophilic acylation of esters by acid chlorides mediated by samarium diiodide: Formation and use of samarium enediolates.

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7183-7186

  Machrouhi, Fouzia ^a   Namy, Jean Louis ^a   Kagan, Henri B ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DIKETONE; KETOL;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030695424     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01727-9     Document Type: Article

References (10)

1. Machrouhi, F.; Hamann, B.; Namy, J.-L.; Kagan, H.B. Synlett, 1996, 633-634.
2. 2, led to about 50% of α-ketol and unreacted starting material..
3. Souppe, J.; Namy, J.-L.; Kagan, H.B. Tetrahedron Lett., 1984, 25, 2869-2872.
4. 4 the crude material is purified by flash chromatography on silica gel.
5. Coupling between samarium enediolates and aldehydes has been previously reported, see ref. 6.
6. Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Chem. Lett., 1993, 959-962.
7. Collin, J.; Namy, J.-L.; Dallemer, F.; Kagan, H.B. J. Org. Chem., 1991, 56, 3118-3122.
8. The reaction of acyl lithium species on esters at -110°C giving α-diketones has been described, see ref. 9
9. Seyferth, D.; Weinstein, R.M.; Wang, W.-L. J. Org. Chem., 1983, 48, 1146-1147.
10. Takeuchi, S.; Miyoshi, N.; Hirata, K.; Hayashida, H.; Ohgo, Y. Bull. Chem. Soc. Jpn., 1992, 65, 2001-2003.