Dehydrative alkylation of alcohols with triethyl methanetricarboxylate under Mitsunobu conditions

Tetrahedron

Volumn 52, Issue 40, 1996, Pages 13007-13016

  Cravotto, Giancarlo ^a   Giovenzana, Giovanni B ^b   Sisti, Massimo ^b   Palmisano, Giovanni ^a  

^a UNIVERSITY OF TURIN   (Italy)

^b Dipto di Chim Organ e Industriale   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 16044375297     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00781-8     Document Type: Article

References (33)

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2. 2. a) Mitsunobu, O. Synthesis 1981, 1;
3. b) Hughes, D.L. Org.Reactions 1972, 42, 335;
4. c) Hughes, D.L. Org.Prep.Proc.Int. 1996, 28, 129.
5. 3. a) Hughes, D.L.; Reamer, R.A.; Bergan, J.J.; Grabowski, E.J.I. J.Am.Chem.Soc. 1988, 110, 6487;
6. b) Camp, D.; Jenkins, I.D. J.Org.Chem. 1989, 54, 3045;
7. c) Camp, D.; Jenkins, I.D. ibid. 1989, 54, 3049;
8. d) Camp, D.; Jenkins, I.D.Aust.J.Chem. 1992, 45, 47;
9. e) Macor, J.E.; Wehner, J.M. Heterocycles 1993, 35, 349.
10. 4. Falck, J.R.; Yu, J.; Cho, H.-S. Tetrahedron Lett. 1994, 35, 5997.
11. 5. Diethyl malonate reacts with benzyl alcohol through the agency of TPP-DEAD in only 2-3% yield (Tsunoda, T.; Yamamiya, Y.; Ito, S. Tetrahedron Lett. 1993, 34, 1639).
12. 6. See for example. Aesa, M.C.; Baan, G.; Novak, L.; Szantay, C. Synthetic Commun. 1996, 26, 909 and references cited.
13. 7. Yu, J.; Falck, J.R.; Mioskowski, C. J.Org.Chem.1992, 57, 3757.
14. 8. Yu, J.; Lai, J.Y., Falck, J.R. SYNLETT. 1995, 1127.
15. 9. For a review on the chemistry of methanetricarboxylate esters: Newkome, G.R.; Baker, G.R. Org.Prep. Proc.Int. 1986, 18, 119.
16. 10. Guthrie, J.P. Can.J.Chem. 1979, 57, 1177.
17. 11. Newkome, G.R.; Yao, Z.-Q.; Baker, G.R.; Gupta, V.K. J.Org.Chem. 1985, 50, 2003.
18. 12. Padgett, H.C.; Csendes, I.G.; Rapoport, H. J.Org.Chem. 1979, 44, 3492.
19. 13. Bohme, H.; Hafner, L. Chem.Ber. 1966, 99, 281.
20. 14. Arct, B.; Prelicz, D.; Witek, H. Rocz.Chem. 1967, 41, 683 (Chem.Abstr. 1967, 67, 54098q).
21. 14. Arct, B.; Prelicz, D.; Witek, H. Rocz.Chem. 1967, 41, 683 (Chem.Abstr. 1967, 67, 54098q).
22. 3P in lieu of TPP and the use of DIAD (diisopropyl azodicarboxylate) in lieu of DEAD.
23. 16. Throughout this paper, a and b designate the starting material and the expected Mitsunobu product, respectively.
24. 17. Wada, M.; Mitsunobu, O. Tetrahedron Lett. 1972, 1279.
25. 18. Mitsunobu reaction on chiral non-racemic p-methoxy benzyl alcohols or alkyl furylmethanols are prone to esterification with substantial racemisation due to the stability of the incipient carbocation which promotes the unimolecular pathway (Brown, R.F.C.; Jackson, W.R.; McCarthy, T.D.; Tetrahedron Lett. 1993, 34, 1195; Warmerdam, E.G.J.C.; Brussee, J.; Kruse, C.G.; van der Gen. A. Tetrahedron Lett. 1993, 34, 1063).
26. 18. Mitsunobu reaction on chiral non-racemic p-methoxy benzyl alcohols or alkyl furylmethanols are prone to esterification with substantial racemisation due to the stability of the incipient carbocation which promotes the unimolecular pathway (Brown, R.F.C.; Jackson, W.R.; McCarthy, T.D.; Tetrahedron Lett. 1993, 34, 1195; Warmerdam, E.G.J.C.; Brussee, J.; Kruse, C.G.; van der Gen. A. Tetrahedron Lett. 1993, 34, 1063).
27. 19. Synfacial attack i.e., the nucleophile enters from the same side as the leaving group departs (Jefford, C.W.; Sweeney, A.; Hill, D.T., Delay, F.; Helv.Chim.Acta 1971, 54, 1691).
28. 20. a) Streitwieser, A. In ' Molecular Orbital Theory for Organic Chemists' Wiley, New York, N.Y., 1961;
29. b) Herndon, W.C., Feuer, J. J.Org.Chem. 1968, 33, 417;
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31. 21. For related examples, see Ref. 20c; Yamamoto, F.; Hiroyuki, M.; Oae, S. Heterocycles 1975, 3, 1.
32. 22. Kurihara, T.; Sugizaki, M.; Kime, I.; Wada, M.; Mitsunobu, O.; Bull. Chem. Soc. Jpn 1981, 54, 2107.
33. 23. Rakus, K.; Verevkin, S.P.; Keller, M.; Beckhaus, H.-D.; Rüchardt, C. Liebigs Ann. 1995, 1483.