Diastereoselective synthesis of dimethyl cyclopropane-1,1-dicarboxylates from a γ-alkoxy-alkylidene malonate and sulfur and phosphorus ylides

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1437-1440

  Krief, Alain ^a   Provins, Laurent ^a   Froidbise, Alexandre ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; GLYCERALDEHYDE; MALONIC ACID DERIVATIVE; PHOSPHORUS DERIVATIVE; SULFUR DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; SYNTHESIS;

EID: 0032510368     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10822-X     Document Type: Article

References (36)

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24. (b) piperidine, 20°C, 24h (30% yield)
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31. 11. We used for that purpose a chiral column Chiralcel OD-H from Daicel Chemical Industries, 0.5×25 cm, solvent : hexane-isopropanol : 97/3, pressure : 47 bar, 1ml / min., UV detection 254 nm, (I)-5 : Rt = 17.8 min. ; (d)-5 : Rt = 19.2 min..
32. 12b was unsuccessful with PCC even when carried out with AcONa as a buffer, since it provides an intractable mixture of compounds. Swern oxidation leads to the desired aldehyde (d,l)-4 which cannot be fully purified. That is the reason why the yield of (d,l)-5 was so low
33. (b) Newman, M. S.; Renall, M. J. Am. Chem. Soc. 1945, 67, 1621.
34. 13b that dimethyl ethylidene malonate reacts with isopropylidene triphenyl phosphorane (generated from isopropyl triphenylphosphonium iodide and n-Buli in THF, 20°C, 1 h) to provide the corresponding dimethyl 2-ethyl-cyclopropane-1,1-dicarboxylate (i) in 44 % yield when the reaction is carried out in THF (20°C, 24 h) (ii) in 14% yield when performed in the same solvent but at higher temperature (80°C, 24h) and (iii) in 70 % yield if performed in a THF-DMSO mixture (80°C, 6h)
35. (b) Unpublished results from our laboratory; De Vos M.-J. Research Report, July 1984.
36. Si according to the same procedure (Scheme 4).