Stereoselective synthesis of tetrahydrofurans and tetrahydropyrans by acid-catalyzed cyclization of hydroxy selenides and hydroxy sulfides

Tetrahedron

Volumn 55, Issue 49, 1999, Pages 14097-14110

  Gruttadauria, Michelangelo ^a   Lo Meo, Paolo ^a   Noto, Renato ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; HYDROXYL GROUP; SELENIDE; SULFIDE; TETRAHYDROFURAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLIZATION; ENERGY; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033520951     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00876-5     Document Type: Article

References (41)

1. 1. (a) Harmange J. C.; Figadere B. Tetrahedron: Asymmetry, 1993, 4, 1711-1754;
2. (b) Bovin T. L. B. Tetrahedron, 1987, 43, 3309-3362;
3. (c) Bartlett P. A. Tetrahedron, 1980, 36, 2-72;
4. (d) Bartlett P. A. Asymetric Synthesis, Vol. III, Chap. 6, Academic Press: Florida, 1984; 411-454;
5. (e) Semple J. E.; Jouillie M. Heterocycles, 1980, 14, 1825-1870.
6. 2. For representative recent example of tetrahydrofuran and tetrahydropyran synthesis see; (a) McIntyre S.; Sansbury F. H.; Warren S. Tetrahedron Lett., 1991, 32, 5409-5412;
7. (b) Kang S. H.; Lee S. B. Tetrahedron Lett., 1993, 34, 7579-7582;
8. (c) Banks J. M.; Knight D. W.; Seaman C. J.; Weingarten G. G. Tetrahedron Lett., 1994, 35, 7259-7262;
9. (d) Walkup R. D.; Kim S. W. J. Org. Chem., 1994, 59, 3433-3441;
10. (e) Lipshutz B. H.; Gross T. J. Org. Chem., 1995, 60, 3572-3573;
11. (f) Bratt K.; Garavelas A.; Perlmutter P.; Westman G. J. Org. Chem., 1996, 61, 2109-2117;
12. (g) Eames J.; Jones R. V. H.; Warren S. Tetrahedron Lett., 1996, 37, 4823-4826;
13. (h) Andrey O.; Glanzmann C.; Landais Y.; Parra-Rapado L. Tetrahedron, 1997, 53, 2835-2854;
14. (i) Mori Y. Chem. Eur. J., 1997, 3, 849-852;
15. (j) Koert U.; Stein M.; Wagner H. Chem. Eur. J., 1997, 3, 1170-1180 and pertinent references within these articles.
16. 3. (a) Arista L.; Gruttadauria M.; Thomas E. J. Synlett, 1997, 627-628;
17. (b) Arista L.; Gruttadauria M.; Noto R. Heterocycles, 1998, 48, 1325-1330;
18. (c) Gruttadauria M.; Lo Meo P.; Noto R. Tetrahedron 1999, 55, 4769-4782.
19. 4. Krief A.; Laboureur J. L.; Dumont W.; Labar D. Bull. Soc. Chim. Fr., 1990, 127, 681-696.
20. 5. Mihelich E. D. J. Am. Chem. Soc., 1990, 112, 8995-8997.
21. 6. (a) Eames J.; de las Heras M. A.; Jones R. V. H.; Warren S. Tetrahedron Lett., 1996, 37, 4581-4584;
22. (b) Eames J.; Warren S. Tetrahedron Lett., 1996, 37, 3525-3528;
23. (c) Bird P.; Eames J.; Fallis A. G.; Jones R. V. H.; Roddis M.; Sturino C. F.; O'Sullivan S.; Warren S.; Westwell M. S.; Worrall J. Tetrahedron Lett., 1995, 36, 1909-1912;
24. (d) Djakovitch L.; Eames J.; Jones R. V. H.; McIntyre S.; Warren S. Tetrahedron Lett., 1995, 36, 1723-1726;
25. (e) Sansbury F. H.; Warren S. Tetrahedron Lett., 1992, 33, 539-542;
26. (f) McIntyre S.; Warren S. Tetrahedron Lett., 1990, 31, 3457-3460.
27. 7. Mihelich E. D.; Daniels K.; Eickhoff D. J. J. Am. Chem. Soc., 1981, 103, 7690-7692.
28. 8. Wirth T. Tetrahedron , 1999, 55, 1-28; Wirth T.; Fragale G; Spichty M. J. Am. Chem. Soc., 1998, 120, 3376-3381.
29. 8. Wirth T. Tetrahedron , 1999, 55, 1-28; Wirth T.; Fragale G; Spichty M. J. Am. Chem. Soc., 1998, 120, 3376-3381.
30. 9. Nicolaou K. C.; Petasis N. A.; Claremon D. A. Tetrahedron, 1985, 41, 4835-4841.
31. 10. Rémion J.; Dumont W.; Krief A. Tetrahedron Lett., 1976, 1385-1388.
32. 11. Lowry T. H.; Richardson K. S. Mechanism and Theory in Organic Chemistry, Harper & Row, New York; Third Ed., 1987, 370; Pearson R. G.; Sobel H.; Songstad J. J. Am. Chem. Soc., 1968, 90, 319.
33. 11. Lowry T. H.; Richardson K. S. Mechanism and Theory in Organic Chemistry, Harper & Row, New York; Third Ed., 1987, 370; Pearson R. G.; Sobel H.; Songstad J. J. Am. Chem. Soc., 1968, 90, 319.
34. 12. Dewar M. J. S. et al, J. Am. Chem. Soc., 1985, 107, 3902-3909.
35. 13. Stewart J. J. P. J. Comp. Chem., 1989, 10, 210-220; Stewart J. J. P. J. Comp. Chem., 1991, 12, 320-341.
36. 13. Stewart J. J. P. J. Comp. Chem., 1989, 10, 210-220; Stewart J. J. P. J. Comp. Chem., 1991, 12, 320-341.
37. * is the minimum basis set to use; see: Iwakoa M.; Tomoda S., J. Org. Chem., 1995, 60, 5299-5302; Iwakoa M.; Tomoda S., J. Am. Chem. Soc., 1996, 118, 8077-8084.
38. * is the minimum basis set to use; see: Iwakoa M.; Tomoda S., J. Org. Chem., 1995, 60, 5299-5302; Iwakoa M.; Tomoda S., J. Am. Chem. Soc., 1996, 118, 8077-8084.
39. * predicts for such a conformation an absolute energy at 0 K of -3037.54982959 Hartree.
40. *, differently from semiempiricals, predicts in MeCHSePh the phenyl group in an anti position with respect to the methyl group.
41. 17. Gaussian 98, Revision A.6; Frisch M. J.; Trucks G. W.; Schlegel H. B.; Scuseria G. E.;. Robb M. A; Cheeseman J. R.; Zakrzewski V. G.; Montgomery J. A. Jr.; Stratmann R. E.; Burant J. C.; Dapprich S.; Millam J. M.; Daniels A. D.; Kudin K. N.; Strain M. C.; Farkas O.; Tomasi J.; Barone V.; Cossi M.; Cammi R.; Mennucci B.; Pomelli C.; Adamo C.; Clifford S.; Ochterski J.; Petersson G. A.; Ayala P. Y.; Cui Q.; Morokuma K.; Malick D. K.; Rabuck A. D.; Raghavachari K.; Foresman J. B.; Cioslowski J.; Ortiz J. V.; Stefanov B. B.; Liu G.; Liashenko A.; Piskorz P.; Komaromi I.; Gomperts R.; Martin R. L.; FoxD. J.; Keith T.; Al-Laham M. A.; Peng C. Y.; Nanayakkara A.; Gonzalez C.; Challacombe M.; Gill P. M. W.; Johnson B.; Chen W.; Wong M. W.; Andres J. L.; Gonzalez C.; Head-Gordon M.; Replogle E. S.; Pople J. A.; Gaussian, Inc., Pittsburgh PA, 1998.