A study of the intramolecular cyclization reactions of some derivatives of 3-arylsulfonyl cycloalkanols

Tetrahedron Letters

Volumn 37, Issue 38, 1996, Pages 6827-6830

  Gonzales, Stephen S ^a   Jacobs, Hollie K ^a   Juarros, LuAnne E ^a   Gopalan, Aravamudan S ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANOL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030590412     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01535-3     Document Type: Article

References (29)

1. 1. Portions of this work were presented at the 209th National ACS meeting, Anaheim, Apr. 2-6, 1995, ORGN 252.
2. 2. Simpkins, N. S. Sulfones in Organic Synthesis, Pergamon Press: Oxford 1993.
3. 3. For some recent examples of intramolecular cyclization reactions involving sulfones see: a) Suh, Y.-G.; Koo, B.-A.; Kim, E.-N.; Choi, N.-S. Tetrahedron Lett. 1995, 36, 2089.
4. b) Grimm, E. L.; Coutu, M. L.; Trimble, L. A. Tetrahedron Lett. 1993, 34, 7017.
5. c) Date, M.; Watanabe, M.; Furukawa, S. Chem. Pharm. Bull. 1990, 38, 902.
6. d) Grimm, E. L.; Levac, S.; Trimble, L. A. Tetrahedron Lett. 1994, 35, 6847.
7. e) Carretero, J. C.; Arrayás, R. G. J. Org. Chem. 1995, 60, 6000.
8. f) Anderson, M. B.; Lamothe, M.; Fuchs, P. L. Tetrahedron Lett. 1991, 32, 4457.
9. g) Funk, R. L.; Bolton, G. L.; Brummond, K. M.; Ellestad, K. E.; Stallman, J. B. J. Am. Chem. Soc. 1993, 115, 7023.
10. 4. a) Craig, D.; Ikin, N. J.; Mathews, N.; Smith, A. M. Tetrahedron Lett. 1995, 36, 7531.
11. b) Li, C.; Fuchs, P. L. Synlett, 1994, 629.
12. c) Carretero, J. C.; Arrayás, R. G.; Storch de Gracia, I. Tetrahedron Lett. 1996, 37, 3379.
13. 5. Jacobs, H. K.; Gopalan, A. S. J. Org. Chem. 1994, 59, 2014.
14. 6. Jacobs, H. K.; Mueller, B. H.; Gopalan, A. S. Tetrahedron 1992, 48, 8891.
15. 7. Gopalan, A. S; Jacobs, H. K. Tetrahedron Lett. 1990, 31, 5575.
16. 8. For some recent uses of hydroxysulfones in synthesis see: a) Solladié, G.; Lohse, O. J. Org. Chem. 1993, 58, 4555.
17. b) Robin, S.; Huet, F. Tetrahedron Lett. 1993, 34, 2945.
18. c) Yamamoto, K.; Shimizu, M.; Yamada, S.; Iwata, S.; Hoshino, O. J. Org. Chem. 1992, 57, 33.
19. d) Alzerreca, A.; Aviles, M.; Collazo, L.; Prieto, A. J. Heterocycl. Chem. 1990, 27, 1729.
20. e) Jung, J. H.; Lee, J. W.; Oh, D. Y. Tetrahedron Lett. 1995, 36, 923.
21. 9. Fayos, J.; Clardy, J.; Dolby, L. J.; Farnham, T. J. Org. Chem. 1977, 42, 1349.
22. 10. For a discussion on the factors governing the stereochemistry of the reduction of substituted cycloalkanones see: Ravikumar, K. S.; Chandrasekaran, S. J. Org. Chem. 1996, 61, 826.
23. 11. Rothberg, I.; Sundoro, B.; Balanikas, G.; Kirsch, S. J. Org. Chem. 1983, 48, 4345.
24. 12. Spectroscopic and elemental analysis of all compounds are in agreement with their assigned structures.
25. 13. The cyclization reaction can be carried out using 1.2 eq of LHMDS. However, it was experimentally convenient to use excess base to ensure complete deprotonation of the substrate.
26. 14. Boche, G. Angew. Chem. Int. Ed. Engl. 1989, 25, 277.
27. 15. a) Iwata, C.; Tanaka, A.; Mizuno, H.; Miyashita, K. Heterocycles, 1990, 31, 987.
28. b) Meinwald, J.; Frauenglass, E. J. Am. Chem. Soc. 1960, 82, 5235.
29. 16. For an enantioselective approach to the synthesis of γ-hydroxy unsaturated cyclic sulfones see: Trost, B. M.; Organ, M. G.; O'Doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662 and references cited therein.