Synthesis and alkylation of cyclopentane β-ketoxime sulfones. α,α-methylation-alkynylation of cyclopentanone

Tetrahedron

Volumn 52, Issue 20, 1996, Pages 6903-6912

  Trost, Barry M ^a   Barrett, David ^a,b  

^a STANFORD UNIVERSITY   (United States)

^b ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029932367     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00325-0     Document Type: Article

References (25)

1. For reviews of the utility of sulfones in synthesis, see (a) Trost, B.M. Bull. Chem. Soc. Jpn. 1988, 61, 107.
2. (b) Magnus, P.D. Tetrahedron 1977, 33, 2019.
3. For a review of methods of desulfonylation, see: Chap. 9 in Simpkins, N.S. Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993. See also: Petrini, M.; Giovannini, R. Synlett. 1995, 973.
4. For a review of methods of desulfonylation, see: Chap. 9 in Simpkins, N.S. Sulphones in Organic Synthesis, Pergamon Press, Oxford, 1993. See also: Petrini, M.; Giovannini, R. Synlett. 1995, 973.
5. 4-mediated desulfonylation of β-ketoxime sulfone intermediates employed in a prostaglandin synthesis, see: (a) Donaldson, R.E.; Fuchs, P.L. J. Am. Chem. Soc. 1981, 103, 2108.
6. (b) Donaldson, R.E.; Saddler, J.C.; Byrn, S.; McKenzie, A.T.; Fuchs, P.L. J. Org. Chem., 1983, 48, 2167.
7. For the preparation of some β-ketoxime sulfones, including 2a (oxime configuration unknown), as intermediates for pesticides and pharmaceuticals, see: Beger, J.; Neumann, R. East German Patent, DD 235 254 A1, 1986 (Chem. Abst., 105, 226042p).
8. Vinyl nitroso species are versatile intermediates that participate in a variety of bond-forming reactions. For a review see: Gilchrist, T.L., Chem. Soc. Rev. 1983, 1, 53. For the generation and trapping of nitroso olefins from α-bromo and α-chloro ketoximes see: (a) Corey, E.J.; Petrzilka, M.; Ueda, Y. Tetrahedron Lett. 1975, 49, 4343, and Helv. Chim. Acta 1977, 70, 2294.
9. Vinyl nitroso species are versatile intermediates that participate in a variety of bond-forming reactions. For a review see: Gilchrist, T.L., Chem. Soc. Rev. 1983, 1, 53. For the generation and trapping of nitroso olefins from α-bromo and α-chloro ketoximes see: (a) Corey, E.J.; Petrzilka, M.; Ueda, Y. Tetrahedron Lett. 1975, 49, 4343, and Helv. Chim. Acta 1977, 70, 2294.
10. Vinyl nitroso species are versatile intermediates that participate in a variety of bond-forming reactions. For a review see: Gilchrist, T.L., Chem. Soc. Rev. 1983, 1, 53. For the generation and trapping of nitroso olefins from α-bromo and α-chloro ketoximes see: (a) Corey, E.J.; Petrzilka, M.; Ueda, Y. Tetrahedron Lett. 1975, 49, 4343, and Helv. Chim. Acta 1977, 70, 2294.
11. (b) Denmark, S.E.; Dappen, M.S. J. Org. Chem. 1984, 49, 798 and references cited therein.
12. For examples of sulfones as leaving groups in C-C bond-forming reactions see: (a) Trost, B.M.; Schmuff, N.R.; Miller, M.J. J. Am. Chem. Soc. 1980, 102, 5979.
13. (b) Julia, M.; Verpeaux, J.N. Tetrahedron 1983, 39, 3289.
14. Trost, B.M.; Adams, B.R. J. Am. Chem. Soc. 1983, 105, 4849.
15. Trost, B.M.; Ghadiri, M.R. J. Am. Chem. Soc. 1984, 106, 7260.
16. (a) Trost, B.M.; Vincent, J.E. J. Am. Chem. Soc. 1980, 102, 5680.
17. (b) Trost, B.M.; Salzmann, T.N.; Hiroi, K. J. Am. Chem. Soc. 1976, 98, 4887.
18. (c) Trost, B.M.; Curran, D.P. Tetrahedron Lett. 1981, 22, 1287.
19. For some applications of 1a in synthesis see: (a) Trost, B.M.; Remuson, R. Tetrahedron Lett. 1983, 24, 1129.
20. (b) Trost, B.M.; Urabe, H. J. Am. Chem. Soc. 1990, 112, 4982.
21. Bunnell, C.A.; Fuchs, P.L. J. Org. Chem. 1977, 42, 2614.
22. For the syn-sulfenylation of oxime dianions see: (a) Hiroi, K.; Otsuka, M.; Sato, S. Chem. Lett. 1985, 1907.
23. (b) Hiroi, K.; Arinaga, Y.; Umemura, M. Annu. Rep. Tohoku Coll. Pharm. 1987, 34, 85 (in Japanese) (Chem. Abst., 110, 192633t).
24. (b) Hiroi, K.; Arinaga, Y.; Umemura, M. Annu. Rep. Tohoku Coll. Pharm. 1987, 34, 85 (in Japanese) (Chem. Abst., 110, 192633t).
25. Timms, G.H.; Wildsmith, E. Tetrahedron Lett. 1971, 2, 195.