Highly efficient selective monohydrolysis of dialkyl malonates and their derivatives

Tetrahedron Letters

Volumn 49, Issue 28, 2008, Pages 4434-4436

  Niwayama, Satomi ^a   Cho, Hanjoung ^a   Lin, Chunlei ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

Desymmetrization; Half ester; Hydrolysis; Monoalkyl malonate derivatives

Indexed keywords

ACETONITRILE; ESTER DERIVATIVE; MALONIC ACID DERIVATIVE; POTASSIUM HYDROXIDE; TETRAHYDROFURAN;

ARTICLE; CHEMICAL STRUCTURE; DECARBOXYLATION; HYDROLYSIS; HYDROPHOBICITY;

EID: 44649189776     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.007     Document Type: Article

References (34)

1. For example,. Bulychev A., Bellettini J.R., O'Brien M., Crocker P.J., Samama J.-P., Miller M.J., and Mobashery S. Tetrahedron 56 (2000) 5719-5728
2. Bihovsky R., and Pendrak I. Bioorg. Med. Chem. Lett. 6 (1996) 1541-1542
3. Horikawa M., and Shirahama H. Synlett (1996) 95-96
4. Keum G., Hwang C.H., Kang S.B., Kim Y., and Lee E. J. Am. Chem. Soc. 127 (2005) 10396-10399
5. Kim H.-J., and Lindsey J. J. Org. Chem. 70 (2005) 5475-5486
6. Knoelker H.-J., and Wolpert M. Tetrahedron Lett. 38 (1997) 533-536
7. Marcaccini S., Pepino R., Pozo M.C., Basurto S., Garcia-Valverde M., and Torroba T. Tetrahedron Lett. 45 (2004) 3999-4001
8. List B., Doehring A., Hechavarria Fonseca M.T., Job A., and Rios Torres R. Tetrahedron 62 (2006) 476-482
9. Balasubramanian T., and Lindsey J.S. Tetrahedron 55 (1999) 6771-6784
10. Hudson R.D.A., Osborne S.A., and Stephenson G.R. Synlett (1996) 845-846
11. Ashton M.J., Hills S.J., Newton C.G., Taylor J.B., and Tondu S.C.D. Heterocycles 28 (1989) 1014-1035
12. Williams D.R., Kammler D.C., and Goundry R.F. Heterocycles 67 (2006) 555-559
13. Strube, R.E. Organic Synthesis; Wiley: New York, NY, 1963; Collect. Vol. 4, pp 417-419.
14. Grakauskas V., and Guest A.M. J. Org. Chem. 43 (1978) 3485-3488
15. Hutchinson, C. R.; Nakane, M.; Gollman, H.; Knutson, P.L. Organic Synthesis; Wiley: New York, NY, 1990; Collect. Vol. 7, pp 323-326.
16. For example,. Corey E.J. J. Am. Chem. Soc. 74 (1952) 5897-5905
17. Vecchi A., and Melone G.J. J. Org. Chem. 24 (1959) 109-110
18. Westermann J., Schneider M., Platzek J., and Petrov O. Org. Process Res. Dev. 11 (2007) 200-205
19. de Meijere A., Ernst K., Zuck B., Brandl M., Kozhushkow S.I., Tamm M., Yufit D.S., Howard J.A.K., and Labahn T. Eur. J. Org. Chem. 11 (1999) 3105-3115
20. De Kimpe N., Boeykens M., and Tehrani K.A. J. Org. Chem. 59 (1994) 8215-8219
21. Robertson A., and Sandrock W.F. J. Chem. Soc. (1933) 1617-1618
22. Eaton P.E., Nordari N., Tsanaktsidis J., and Upadhyaya S.P. Synthesis (1995) 501-502
23. Rigo B., Fasseur D., Cauliez P., and Couturier D. Tetrahedron Lett. 30 (1989) 3073-3076
24. Junek H., Ziegler E., Herzog U., and Kroboth H. Synthesis (1976) 332-334
25. Duthaler R. Helv. Chim. Acta 66 (1983) 1475-1492
26. Ozaki E., Uragaki T., Sakashita K., and Sakimae A. Chem. Lett. (1995) 539-540
27. Krapcho A.P., Jahngen Jr. E.G.E., and Kashdan D.S. Tetrahedron Lett. 15 (1974) 2721-2723
28. Niwayama S. J. Org. Chem. 65 (2000) 5834-5836
29. 4. This extract was concentrated in vacuo and purified by silica gel column chromatography with hexane-ethyl acetate (3:1) and then ethyl acetate as typical eluents to afford monomethyl malonate.
30. Niwayama S., and Rimkus A. Bull. Chem. Soc. Jpn. 78 (2005) 498-500
31. We are finding a similar tendency in selective monohydrolysis of other symmetric or non-symmetric diesters. These results will be published in due course.
32. We are investigating further mechanistic studies to detect potential intermediates by physicochemical techniques.
33. Niwayama S., Wang H., Hiraga Y., and Clayton J.C. Tetrahedron Lett. 48 (2007) 8757-8760
34. 4: C, 64.85; H, 6.35. Found: C, 65.17; H, 6.61.