Synthesis of Succinic Diesters via Reductive Coupling of α-Haloesters Using Samarium (II) Iodide and HMPA

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 801-804

  Balaux, Élise ^a   Ruel, Réjean ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

SUCCINIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030029670     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02299-6     Document Type: Article

References (20)

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15. 13C NMR, MS and combustion analyses.
16. 4 anh.), filtered and evaporated. Flash-chromatography (EtOAc-hexane (1: 20)) of the residue gave 2a (162 mg, 59%) along with 1a (114 mg).
17. Before quenching the reaction, adding bromoacetate 1a to the mixture (step ii, Method C) in molar quantity equivalent to that of 5 (ca. 60% Method A and 40% Method B) did not result in a complete conversion 1a to 2a. Because the polarity of compounds 1,2 and 3 is similar, adding benzaldehyde (see 5 → 7) before work-up represents a practical alternative to sometimes difficult chromatographic separations.
18. 3CN).
19. Spanagel, E. W.; Carothers, W. H. J. Am. Chem. Soc. 1935, 57, 929.
20. The synthesis of 8 membered-ring dilactone has been reported: Lee, E.; Lee, D. S.; Lee, K. H.; Choi, I. S. Bull. Korean Chem. Soc. 1992, 13, 470.