Propylene glycol cyclic sulfate as a substitute for propylene oxide in reactions with acetylides

Synthetic Communications

Volumn 33, Issue 4, 2003, Pages 633-640

  Bates, Roderick W ^a   Maiti, Tushar B ^b  

^a CHULABHORN RESEARCH INSTITUTE   (Thailand)

^b UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LITHIUM DERIVATIVE; PROPYLENE GLYCOL; PROPYLENE OXIDE;

ARTICLE; CHEMICAL ANALYSIS; CHROMATOGRAPHY; HYDROLYSIS; MASS SPECTROMETRY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037231863     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120015819     Document Type: Article

References (38)

1. (a) Gorzynski Smith, J. Synthesis 1984, 629;
2. (b) Garratt, P.J. Comprehensive Organic Synthesis; Trost, B.M., Ed.; Pergamon: Oxford, 1991; Vol. 3, 277.
3. Brandsma, L. Preparative Acetylenic Chemistry; Elsevier: Amsterdam, 1988; 40.
4. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391; see also: Eis, M.J.; Wrobel, J.E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693; Cink, R.D.; Forsyth, C.J. J. Org. Chem. 1995, 60, 8122; Ooi, T.; Kagashima, N.; Ichikawa, I.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 3328.
5. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391; see also: Eis, M.J.; Wrobel, J.E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693; Cink, R.D.; Forsyth, C.J. J. Org. Chem. 1995, 60, 8122; Ooi, T.; Kagashima, N.; Ichikawa, I.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 3328.
6. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391; see also: Eis, M.J.; Wrobel, J.E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693; Cink, R.D.; Forsyth, C.J. J. Org. Chem. 1995, 60, 8122; Ooi, T.; Kagashima, N.; Ichikawa, I.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 3328.
7. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391; see also: Eis, M.J.; Wrobel, J.E.; Ganem, B. J. Am. Chem. Soc. 1984, 106, 3693; Cink, R.D.; Forsyth, C.J. J. Org. Chem. 1995, 60, 8122; Ooi, T.; Kagashima, N.; Ichikawa, I.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 3328.
8. Fried, J.; Lin, C.H.; Ford, S.H. Tetrahedron Lett. 1969, 1379.
9. For examples of reactions of propylene oxide with acetylides, see: (a) Seebach, D.; Seidel, W. Tetrahedron Lett. 1982, 23, 159; (b) Hillis, L.R.; Ronald, R.C. J. Org. Chem. 1985, 50, 470; (c) Nokamai, J.; Taniguchi, T.; Ogawa, Y. Chem. Lett. 1995, 43.
10. For examples of reactions of propylene oxide with acetylides, see: (a) Seebach, D.; Seidel, W. Tetrahedron Lett. 1982, 23, 159; (b) Hillis, L.R.; Ronald, R.C. J. Org. Chem. 1985, 50, 470; (c) Nokamai, J.; Taniguchi, T.; Ogawa, Y. Chem. Lett. 1995, 43.
11. For examples of reactions of propylene oxide with acetylides, see: (a) Seebach, D.; Seidel, W. Tetrahedron Lett. 1982, 23, 159; (b) Hillis, L.R.; Ronald, R.C. J. Org. Chem. 1985, 50, 470; (c) Nokamai, J.; Taniguchi, T.; Ogawa, Y. Chem. Lett. 1995, 43.
12. Ellis, M.K.; Golding, B.T. Org. Syn. Coll. 1990, 7, 356; Mori, K.; Senda, S. Tetrahedron 1985, 41, 541.
13. Ellis, M.K.; Golding, B.T. Org. Syn. Coll. 1990, 7, 356; Mori, K.; Senda, S. Tetrahedron 1985, 41, 541.
14. For reviews, see Lohray, B.B. Synthesis 1992, 1035; Lohray, B.B.; Bhusan, V. Adv. Het. Chem. 1997, 68, 90; Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051. For recent examples of C-C bond formation, see Hoye, T.R.; Crawford, K.B. J. Org. Chem. 1994, 59, 520; Baldwin, J.E.; Adlington, R.M.; Gollins, D.W.; Godfrey, C.R.A. Tetrahedron 1995, 51, 5169; Stiasny, H.C. Synthesis 1996, 259.
15. For reviews, see Lohray, B.B. Synthesis 1992, 1035; Lohray, B.B.; Bhusan, V. Adv. Het. Chem. 1997, 68, 90; Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051. For recent examples of C-C bond formation, see Hoye, T.R.; Crawford, K.B. J. Org. Chem. 1994, 59, 520; Baldwin, J.E.; Adlington, R.M.; Gollins, D.W.; Godfrey, C.R.A. Tetrahedron 1995, 51, 5169; Stiasny, H.C. Synthesis 1996, 259.
16. For reviews, see Lohray, B.B. Synthesis 1992, 1035; Lohray, B.B.; Bhusan, V. Adv. Het. Chem. 1997, 68, 90; Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051. For recent examples of C-C bond formation, see Hoye, T.R.; Crawford, K.B. J. Org. Chem. 1994, 59, 520; Baldwin, J.E.; Adlington, R.M.; Gollins, D.W.; Godfrey, C.R.A. Tetrahedron 1995, 51, 5169; Stiasny, H.C. Synthesis 1996, 259.
17. For reviews, see Lohray, B.B. Synthesis 1992, 1035; Lohray, B.B.; Bhusan, V. Adv. Het. Chem. 1997, 68, 90; Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051. For recent examples of C-C bond formation, see Hoye, T.R.; Crawford, K.B. J. Org. Chem. 1994, 59, 520; Baldwin, J.E.; Adlington, R.M.; Gollins, D.W.; Godfrey, C.R.A. Tetrahedron 1995, 51, 5169; Stiasny, H.C. Synthesis 1996, 259.
18. For reviews, see Lohray, B.B. Synthesis 1992, 1035; Lohray, B.B.; Bhusan, V. Adv. Het. Chem. 1997, 68, 90; Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051. For recent examples of C-C bond formation, see Hoye, T.R.; Crawford, K.B. J. Org. Chem. 1994, 59, 520; Baldwin, J.E.; Adlington, R.M.; Gollins, D.W.; Godfrey, C.R.A. Tetrahedron 1995, 51, 5169; Stiasny, H.C. Synthesis 1996, 259.
19. For reviews, see Lohray, B.B. Synthesis 1992, 1035; Lohray, B.B.; Bhusan, V. Adv. Het. Chem. 1997, 68, 90; Byun, H.-S.; He, L.; Bittman, R. Tetrahedron 2000, 56, 7051. For recent examples of C-C bond formation, see Hoye, T.R.; Crawford, K.B. J. Org. Chem. 1994, 59, 520; Baldwin, J.E.; Adlington, R.M.; Gollins, D.W.; Godfrey, C.R.A. Tetrahedron 1995, 51, 5169; Stiasny, H.C. Synthesis 1996, 259.
20. Gao, Y.; Sharpless, K.B. J. Am. Chem. Soc. 1988, 110, 7538.
21. Tomalia, D.A.; Falk, J.C. J. Heterocycl. Chem. 1972, 9, 891; Bates, R.W.; Fernandez-Moro, R.; Ley, S.V. Tetrahedron 1991, 47, 9929; Pais, G.C.G.; Byun, H.-S.; Sadlofsky, J.A.; Bittman, R. J. Org. Chem. 1998, 63, 2560; Fernandes, R.A.; Kumar, P. Tetrahedron 1999, 55, 13445; Gourlain, T.; Wadouachi, A.; Beauére, D. Synthesis 1999, 2, 290. A Payne rearrangement of a hydroxymethyl cyclic sulfate, followed by acetylide attack on the resulting epoxide has been reported: Ko, S.Y. Tetrahedron Lett. 1994, 35, 3601.
22. Tomalia, D.A.; Falk, J.C. J. Heterocycl. Chem. 1972, 9, 891; Bates, R.W.; Fernandez-Moro, R.; Ley, S.V. Tetrahedron 1991, 47, 9929; Pais, G.C.G.; Byun, H.-S.; Sadlofsky, J.A.; Bittman, R. J. Org. Chem. 1998, 63, 2560; Fernandes, R.A.; Kumar, P. Tetrahedron 1999, 55, 13445; Gourlain, T.; Wadouachi, A.; Beauére, D. Synthesis 1999, 2, 290. A Payne rearrangement of a hydroxymethyl cyclic sulfate, followed by acetylide attack on the resulting epoxide has been reported: Ko, S.Y. Tetrahedron Lett. 1994, 35, 3601.
23. Tomalia, D.A.; Falk, J.C. J. Heterocycl. Chem. 1972, 9, 891; Bates, R.W.; Fernandez-Moro, R.; Ley, S.V. Tetrahedron 1991, 47, 9929; Pais, G.C.G.; Byun, H.-S.; Sadlofsky, J.A.; Bittman, R. J. Org. Chem. 1998, 63, 2560; Fernandes, R.A.; Kumar, P. Tetrahedron 1999, 55, 13445; Gourlain, T.; Wadouachi, A.; Beauére, D. Synthesis 1999, 2, 290. A Payne rearrangement of a hydroxymethyl cyclic sulfate, followed by acetylide attack on the resulting epoxide has been reported: Ko, S.Y. Tetrahedron Lett. 1994, 35, 3601.
24. Tomalia, D.A.; Falk, J.C. J. Heterocycl. Chem. 1972, 9, 891; Bates, R.W.; Fernandez-Moro, R.; Ley, S.V. Tetrahedron 1991, 47, 9929; Pais, G.C.G.; Byun, H.-S.; Sadlofsky, J.A.; Bittman, R. J. Org. Chem. 1998, 63, 2560; Fernandes, R.A.; Kumar, P. Tetrahedron 1999, 55, 13445; Gourlain, T.; Wadouachi, A.; Beauére, D. Synthesis 1999, 2, 290. A Payne rearrangement of a hydroxymethyl cyclic sulfate, followed by acetylide attack on the resulting epoxide has been reported: Ko, S.Y. Tetrahedron Lett. 1994, 35, 3601.
25. Tomalia, D.A.; Falk, J.C. J. Heterocycl. Chem. 1972, 9, 891; Bates, R.W.; Fernandez-Moro, R.; Ley, S.V. Tetrahedron 1991, 47, 9929; Pais, G.C.G.; Byun, H.-S.; Sadlofsky, J.A.; Bittman, R. J. Org. Chem. 1998, 63, 2560; Fernandes, R.A.; Kumar, P. Tetrahedron 1999, 55, 13445; Gourlain, T.; Wadouachi, A.; Beauére, D. Synthesis 1999, 2, 290. A Payne rearrangement of a hydroxymethyl cyclic sulfate, followed by acetylide attack on the resulting epoxide has been reported: Ko, S.Y. Tetrahedron Lett. 1994, 35, 3601.
26. Tomalia, D.A.; Falk, J.C. J. Heterocycl. Chem. 1972, 9, 891; Bates, R.W.; Fernandez-Moro, R.; Ley, S.V. Tetrahedron 1991, 47, 9929; Pais, G.C.G.; Byun, H.-S.; Sadlofsky, J.A.; Bittman, R. J. Org. Chem. 1998, 63, 2560; Fernandes, R.A.; Kumar, P. Tetrahedron 1999, 55, 13445; Gourlain, T.; Wadouachi, A.; Beauére, D. Synthesis 1999, 2, 290. A Payne rearrangement of a hydroxymethyl cyclic sulfate, followed by acetylide attack on the resulting epoxide has been reported: Ko, S.Y. Tetrahedron Lett. 1994, 35, 3601.
27. [8] is higher yielding and more convenient. Propylene glycol is appreciably hygroscopic, but it may be conveniently dried by azeotropic removal of water with toluene.
28. Kim, B.M.; Sharpless, K.B. Tetrahedron Lett. 1989, 30, 655.
29. Le Coq, A.; Gorgues, A. Org. Syn. Coll. 1988, 6, 954.
30. [14]
31. [14]
32. [14]
33. [14]
34. For the corresponding epoxide reaction, see Boche, G.; Bigalke, J. Tetrahedron Lett. 1984, 25, 1955.
35. Trost, B.M.; Krause, L.; Portnoy, M. J. Am. Chem. Soc. 1997, 119, 11319.
36. Dale, D.E.; Rhee, C.K. Tetrahedron Lett. 1991, 32, 7165.
37. [7]
38. The rapid formation of a cloudy precipitate indicates that sufficient acid has been added. If the mixture is not opaque, hydrolysis of the hemisulfate does not occur and more acid is required.