Cesium promoted O-alkylation of alcohols for the efficient ether synthesis

Tetrahedron Letters

Volumn 40, Issue 10, 1999, Pages 1843-1846

  Dueno, E E ^a   Chu, F ^a   Kim, S I ^a   Kyung Woon Jung, ^a  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

Cesium carbonate and cesium hydroxide; Hydroxyl protection; Molecular sieves; O alkylation of alcohols; TBAI

Indexed keywords

ALCOHOL DERIVATIVE; ALKYL GROUP; BROMINE DERIVATIVE; CARBONIC ACID DERIVATIVE; CESIUM; ETHER; TETRABUTYLAMMONIUM;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; MOLECULAR STABILITY; SYNTHESIS;

EID: 0033525651     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00083-0     Document Type: Article

References (33)

1. For comprehensive reviews on the ether linkage, see: N. Baggett J.F. Stoddart Comprehensive Organic Chemistry Vol. 1 1979 Pergamon London 799
2. H. Feuer J. Hooz S. Patai The Chemistry of the Ether Linkage 1967 Interscience Publishers New York 445
3. O. Mitsunobu B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 6 1991 Pergamon London 1
4. For oligonucleotides, see: V. Amarnath A.D. Broom Chem. Rev. 77 1977 183
5. For carbohydrates, see: A. Terjung K.-H. Jung R.R. Schmidt Liebigs Ann. 1996 1313
6. and references cited therein A. Lubineau S. Escher J. Alais D. Bonnaffé Tetrahedron Lett. 38 1997 4087
7. For various examples, see: T.W. Greene P.G.M. Wuts Protective Groups in Organic Synthesis 1991 John Wiley & Sons, INC New York Chapter 2
8. W.J. Williamson J. Chem. Soc. 4 1852 106
9. W.J. Williamson J. Chem. Soc. 4 1852 209
10. R.A.W. Johnstone M.E. Rose Tetrahedron 35 1979 2169
11. O.C. Dermer Chem. Rev. 14 1934 385
12. For crown ether, see: H.C. Aspinall N. Greeves W.-M. Lee E.G. McIver P.M. Smith Tetrahedron Lett. 38 1997 4679
13. For metal salts, see: G.M. Whitesides J.S. Sadowski J. Lilburn J. Am. Chem. Soc. 96 1974 2829
14. J. Barluenga L. Alonso-Cires P.J. Campos G. Asensio Synthesis 1983 53
15. T. Das M.S. Shashidhar Carbohydr. Res. 297 1997 243
16. For phase transfer catalysis, see: W.P. Weber G.W. Gokel Phase Transfer Catalysis in Organic Synthesis 1977 Springer-Verlag Berlin 73
17. R.M. Nouguier M. Mchich J. Org. Chem. 50 1985 3296
18. The precedented O -alkylation reactions using cesium bases utilized the relatively reactive substrates including acids and phenols. For such representative examples of cesium promoted alkylations, see: H. Kunz R. Kullmann P. Wernig J. Zimmer Tetrahedron Lett. 33 1992 1969
19. W.H. Kruizinga B. Strijtveen R.M. Kellogg J. Org. Chem. 46 1981 4321
20. T. Sato J. Otera H. Nozaki J. Org. Chem. 57 1992 2166
21. W.H. Kruizinga R.M. Kellogg J. Am. Chem. Soc. 103 1981 5183
22. D.N. Reinhoudt F. de Jong H.P.M. Tomassen Tetrahedron Lett. 1979 2067
23. B.P. Czech A. Czech R.A. Bartsch J. Heterocyclic Chem. 22 1985 1297
24. Two related examples were reported using CsF in the aliphatic ether formation: T. Sato K. Yoshimatsu J. Otera Synlett 1995 843
25. N. Nagashima M. Ohno Chem. Lett. 1987 141
26. B.F. Gisin Helv. Chim. Acta 56 1973 1476
27. G. Dijkstra W.H. Kruizinga R.M. Kellogg J. Org. Chem. 52 1987 4230
28. C. Galli Org. Prep. Proced. Int. 24 1992 287
29. C. Galli L. Mandolini J. Chem. Soc., Chem. Commun. 1982 251
30. M. Crescenzi C. Galli L. Mandolini J. Chem. Soc., Chem. Commun. 1986 551
31. C. Galli L. Mandolini J. Chem. Soc., Perkin Trans. II 1984 1435
32. E.T. Stiller A.H. Stanton J. Finkelstein J.C. Keresztesy K. Folkers J. Am. Chem. Soc. 62 1940 1785
33. W.A. Bonner J. Am. Chem. Soc. 73 1951 3126