Practical synthesis of (E)-α,β-unsaturated esters from aldehydes

Advanced Synthesis and Catalysis

Volumn 347, Issue 11-13, 2005, Pages 1558-1560

  List, Benjamin ^a   Doehring, Arno ^a   Hechavarria Fonseca, Maria T ^a   Wobser, Kathrin ^a   Van Thienen, Hendrik ^a   Torres, Ramon Rios ^a   Galilea, Pedro Llamas ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

, unsaturated esters; (E) stereoselectivity; Atom economy; Doebner Knoevenagel reaction; Malonic acid half esters

Indexed keywords

EID: 27544497003     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505196     Document Type: Article

References (34)

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2. For other approaches to α,β-unsaturated esters from aldehydes, see: a) Claisen-Schmidt-type condensation of aromatic aldehydes: M. Hatsuda, T. Kuroda, M. Seki, Synth. Commun. 2003, 33, 427-434;
3. P. Kisanga, B. D'Sa, J. Verkade, Tetrahedron 2001, 57, 8047-8052;
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9. d) via Peterson-type olefination with ethyl (trimethylsilyl)acetate: H. Taguchi, K. Shimoji, H. Yamamoto, H. Nozaki, Bull. Chem. Soc. Jpn. 1974, 47, 2529-2531;
10. e) from mercaptoacetates: S. Matui, K. Tanaka, A. Kaji, Synthesis 1983, 2, 127-128;
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13. h) from ethyl bromoacetate in the presence of a Te-catalyst, potassium carbonate, sodium bisulfite, and triphenyl phosphite: Z. Z. Huang, S. Ye, W. Sia, Y. Tang, Chem. Commun. 2001, 15, 1384-1385;
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17. l) from ethyl (benzothiazol-2-ylsulfonyl)acetate: P. R. Blakemore, D. K. H. Ho, W. M. Nap, Org. Biomol. Chem. 2005, 3, 1365-1368.
18. For selected alternative approaches to α,β-unsaturated esters, see: a) Heck reaction: I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009-3066;
19. b) cross metathesis: A. K. Chatterjee, F. D. Toste, T.-L. Choi, R. H. Grubbs, Adv. Synth. Cat. 2002, 344, 634-637.
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24. 2 = Et) 10 mmol ca. EUR 5.00, monoethyl malonate, potassium salt 10 mmol ca. EUR 2.00.
25. For the preparation of the ethylmalonic acid and of its potassium salt from diethyl malonate (10 mmol ca. EUR 0.60), see: M. E. Hediger, Bioorg. Med. Chem. 2004, 12, 4995-5010.
26. a) A. T. Carmona, J. Fuentes, I. Robina, E. Rodriguez Garcia, R. Demange, P. Vogel, A. L. Winters, J. Org. Chem. 2003, 68, 3874-3883;
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29. d) for mechanistic studies on this subject, see: E. J. Corey, J. Am. Chem. Soc. 1952, 74, 5897-5905;
30. E. J. Corey, J. Am. Chem. Soc. 1953, 75, 1163-1167.
31. In one report DMAP has been used as a catalyst for the reaction of malonic acid half esters with α,β-unsaturated aldehydes at elevated temperature in pyridine to give the corresponding α,β,γ, δ-unsaturated esters, see: J. Rodriguez, B. Waegell, Synthesis 1988, 534-535.
32. See, for example: R. Lalande, J. Moulines, J. Duboudin, Bull. Soc. Chim. Fr. 1962, 1087-1089;
33. see also see: B. List, in: Modern Aldol Reactions, Vol. 1, (Ed.: R. Mahrwald), Wiley-VCH, Weinhein, Germany, 2004, pp. 161-200.
34. Studiengesellschaft Kohle mbH, Process for the production of olefins from carbonyl compounds. Patent pending.