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Mild and Versatile Potassium Fluoride/Tetrabutylammonium Fluoride Protocol for Ester Hydrolysis
Corresponding Author(s) : Shaik Mustafa
Asian Journal of Chemistry,
Vol. 30 No. 2 (2018): Vol 30 Issue 2
Abstract
A mild and versatile protocol of potassium fluoride/tetrabutylammonium fluoride (KF/TBAF) in aqueous tetrahydrofuran for ester hydrolysis has been developed. The method is applied on variety of aliphatic and aromatic ester moieties bearing acid or base sensitive functional groups. The conditions have been also applied on acetates to yield alcohols. The chirality of optically pure esters remained intact with the conditions of the reaction.
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- C. Hodl, K. Raunegger, R. Strommer, G.F. Ecker, O. Kunert, S. Sturm, C. Seger, E. Haslinger, R. Steiner, W.S.L. Strauss and H.-W. Schramm, J. Med. Chem., 52, 1268 (2009); https://doi.org/10.1021/jm800985z.
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References
C. Hodl, K. Raunegger, R. Strommer, G.F. Ecker, O. Kunert, S. Sturm, C. Seger, E. Haslinger, R. Steiner, W.S.L. Strauss and H.-W. Schramm, J. Med. Chem., 52, 1268 (2009); https://doi.org/10.1021/jm800985z.
V. Theodorou, K. Skobridis,A.G. Tzakos and V. Ragoussis, Tetrahedron Lett., 48, 8230 (2007); https://doi.org/10.1016/j.tetlet.2007.09.074.
C.-G. Zhan, D.W. Landry and R.L. Ornstein,J. Am. Chem. Soc., 122, 1522 (2000); https://doi.org/10.1021/ja993311m.
K. Hori, Y. Ikenaga, K. Arata, T. Takahashi, K. Kasai, Y. Noguchi, M. Sumimoto and H. Yamamoto, Tetrahedron, 63, 1264 (2007); https://doi.org/10.1016/j.tet.2006.11.039.
Y. Izumi, Catal. Today, 33, 371 (1997); https://doi.org/10.1016/S0920-5861(96)00165-4.
Y. Koshikari, A. Sakakura and K. Ishihara, Org. Lett., 14, 3194 (2012); https://doi.org/10.1021/ol301290c.
M.L. James, B. Shen, C.L. Zavaleta, C.H. Nielsen, C. Mesangeau, P.K. Vuppala, C. Chan, B.A. Avery, J.A. Fishback, R.R. Matsumoto, S.S. Gambhir, C.R. McCurdy and F.T. Chin, J. Med. Chem., 55, 8272 (2012); https://doi.org/10.1021/jm300371c.
J.J. D’Amico and F.G. Bollinger, J. Heterocycl. Chem., 25, 1183 (1988); https://doi.org/10.1002/jhet.5570250427.
L. Srikanth, U. Naik and R. Jadhav, Int. J. Pharm. Biosci., 1, 260 (2010).
B.G. Raju, R. Ciabattl, S.I. Maffioli, U. Singh, G. Romano, E. Michelucci, S. Tiseni, G. Candiani, B. Kim and H. O’Dowd, Ramoplanin Derivatives Possessing Antibacterial Activity, US Patent 2006/0211603 A1 (2006).
Y. Yamamoto, Adv. Synth. Catal., 352, 478 (2010); https://doi.org/10.1002/adsc.200900836.
V.T. Perchyonok, S.J. Ryan, S.J. Langford, M.T. Hearn and K.L. Tuck,Synlett, 1233 (2008); https://doi.org/10.1055/s-2008-1072727.
A.J. Fugard, B.K. Thompson, A.M.Z. Slawin, J.E. Taylor and A.D. Smith, Org. Lett., 17, 5824 (2015); https://doi.org/10.1021/acs.orglett.5b02997.
C. Chaulet, C. Croix, J. Basset, M.-D. Pujol and M.-C. Viaus-Massuard, Synlett, 10, 1481 (2010); https://doi.org/10.1055/s-0029-1219918.
M.M. Johnson, J.M. Naidoo, M.A. Fernandes, E.M. Mmutlane, W.A.L. van Otterlo and C.B. de Koning, J. Org. Chem., 75, 8701 (2010); https://doi.org/10.1021/jo101873v.
S.-T. Huang, I.-J. Hsei and C. Chen, Bioorg. Med. Chem., 14, 6106 (2006); https://doi.org/10.1016/j.bmc.2006.05.007.