Observations regarding the first step of the Julia-Lythgoe olefin synthesis

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5283-5286

  Hart, David J ^a   Wu, Wen Lian ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; ALKENE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030598082     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01092-1     Document Type: Article

References (25)

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2. 2. (a) For reviews of this olefination process see: Kocienski, P. J. Chem. Ind. 1981, 548.
3. (b) Kocienski, P. Phosphorus and Sulfur and Related Elements 1985, 24, 97.
4. (c) Kocienski, P. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I. Eds., 1991, 6, 987.
5. (d) Simpkins, N. S. in Sulphones in Organic Synthesis, Tetrahedron Organic Chemistry Series 10; Pergamon Press: London, 1993.
6. 3. Hart, D. J.; Wu, W.-L.; Kozikowski, A. P. J. Am. Chem. Soc. 1995, 117, 9369.
7. 5,6
8. 5. Kocienski, P. J.; Lythgoe, B.; Ruston, S. J. Chem. Soc., Perkin Trans. 1 1978, 829.
9. 6. Achmatowicz, B.; Baranowska, E.; Daniewski, A. R.; Pankowski, J.; Wicha, J. Tetrahedron 1988, 44, 4989.
10. 12
11. 8. McFarland, J. W.; Buchanan, D. N.; J. Org. Chem. 1965, 30, 2003. Tavares, D. F.; Vogt, P. F. Can. J. Chem. 1967, 45, 1519. Kobayashi, T.; Taguchi, T.; Kanuma, N.; Kiekawa, N.; Oshida, J.-V. Tetrahedron Lett. 1981, 22, 4309. Kirk, D. N.; Varley, M. J.; Makin, H. L. J.; Trafford, D. J. H. J. Chem. Soc., Perkin Trans. 1 1983, 2563. Nemoto, H.; Suzuki, K.; Tsubuki, M.; Minemura, K.; Fukumoto, K.; Kametani, T.; Furuyama, H. Tetrahedron 1983, 39, 1123. Fehr, C. Helv. Chim. Acta 1983, 66, 2519. Hanessian, S.; Ugolini, A.; Dube, D.; Hodges, P. J.; Andre, C. J. Am. Chem. Soc. 1985, 108, 2776.
12. 8. McFarland, J. W.; Buchanan, D. N.; J. Org. Chem. 1965, 30, 2003. Tavares, D. F.; Vogt, P. F. Can. J. Chem. 1967, 45, 1519. Kobayashi, T.; Taguchi, T.; Kanuma, N.; Kiekawa, N.; Oshida, J.-V. Tetrahedron Lett. 1981, 22, 4309. Kirk, D. N.; Varley, M. J.; Makin, H. L. J.; Trafford, D. J. H. J. Chem. Soc., Perkin Trans. 1 1983, 2563. Nemoto, H.; Suzuki, K.; Tsubuki, M.; Minemura, K.; Fukumoto, K.; Kametani, T.; Furuyama, H. Tetrahedron 1983, 39, 1123. Fehr, C. Helv. Chim. Acta 1983, 66, 2519. Hanessian, S.; Ugolini, A.; Dube, D.; Hodges, P. J.; Andre, C. J. Am. Chem. Soc. 1985, 108, 2776.
13. 8. McFarland, J. W.; Buchanan, D. N.; J. Org. Chem. 1965, 30, 2003. Tavares, D. F.; Vogt, P. F. Can. J. Chem. 1967, 45, 1519. Kobayashi, T.; Taguchi, T.; Kanuma, N.; Kiekawa, N.; Oshida, J.-V. Tetrahedron Lett. 1981, 22, 4309. Kirk, D. N.; Varley, M. J.; Makin, H. L. J.; Trafford, D. J. H. J. Chem. Soc., Perkin Trans. 1 1983, 2563. Nemoto, H.; Suzuki, K.; Tsubuki, M.; Minemura, K.; Fukumoto, K.; Kametani, T.; Furuyama, H. Tetrahedron 1983, 39, 1123. Fehr, C. Helv. Chim. Acta 1983, 66, 2519. Hanessian, S.; Ugolini, A.; Dube, D.; Hodges, P. J.; Andre, C. J. Am. Chem. Soc. 1985, 108, 2776.
14. 8. McFarland, J. W.; Buchanan, D. N.; J. Org. Chem. 1965, 30, 2003. Tavares, D. F.; Vogt, P. F. Can. J. Chem. 1967, 45, 1519. Kobayashi, T.; Taguchi, T.; Kanuma, N.; Kiekawa, N.; Oshida, J.-V. Tetrahedron Lett. 1981, 22, 4309. Kirk, D. N.; Varley, M. J.; Makin, H. L. J.; Trafford, D. J. H. J. Chem. Soc., Perkin Trans. 1 1983, 2563. Nemoto, H.; Suzuki, K.; Tsubuki, M.; Minemura, K.; Fukumoto, K.; Kametani, T.; Furuyama, H. Tetrahedron 1983, 39, 1123. Fehr, C. Helv. Chim. Acta 1983, 66, 2519. Hanessian, S.; Ugolini, A.; Dube, D.; Hodges, P. J.; Andre, C. J. Am. Chem. Soc. 1985, 108, 2776.
15. 8. McFarland, J. W.; Buchanan, D. N.; J. Org. Chem. 1965, 30, 2003. Tavares, D. F.; Vogt, P. F. Can. J. Chem. 1967, 45, 1519. Kobayashi, T.; Taguchi, T.; Kanuma, N.; Kiekawa, N.; Oshida, J.-V. Tetrahedron Lett. 1981, 22, 4309. Kirk, D. N.; Varley, M. J.; Makin, H. L. J.; Trafford, D. J. H. J. Chem. Soc., Perkin Trans. 1 1983, 2563. Nemoto, H.; Suzuki, K.; Tsubuki, M.; Minemura, K.; Fukumoto, K.; Kametani, T.; Furuyama, H. Tetrahedron 1983, 39, 1123. Fehr, C. Helv. Chim. Acta 1983, 66, 2519. Hanessian, S.; Ugolini, A.; Dube, D.; Hodges, P. J.; Andre, C. J. Am. Chem. Soc. 1985, 108, 2776.
16. 8. McFarland, J. W.; Buchanan, D. N.; J. Org. Chem. 1965, 30, 2003. Tavares, D. F.; Vogt, P. F. Can. J. Chem. 1967, 45, 1519. Kobayashi, T.; Taguchi, T.; Kanuma, N.; Kiekawa, N.; Oshida, J.-V. Tetrahedron Lett. 1981, 22, 4309. Kirk, D. N.; Varley, M. J.; Makin, H. L. J.; Trafford, D. J. H. J. Chem. Soc., Perkin Trans. 1 1983, 2563. Nemoto, H.; Suzuki, K.; Tsubuki, M.; Minemura, K.; Fukumoto, K.; Kametani, T.; Furuyama, H. Tetrahedron 1983, 39, 1123. Fehr, C. Helv. Chim. Acta 1983, 66, 2519. Hanessian, S.; Ugolini, A.; Dube, D.; Hodges, P. J.; Andre, C. J. Am. Chem. Soc. 1985, 108, 2776.
17. 8. McFarland, J. W.; Buchanan, D. N.; J. Org. Chem. 1965, 30, 2003. Tavares, D. F.; Vogt, P. F. Can. J. Chem. 1967, 45, 1519. Kobayashi, T.; Taguchi, T.; Kanuma, N.; Kiekawa, N.; Oshida, J.-V. Tetrahedron Lett. 1981, 22, 4309. Kirk, D. N.; Varley, M. J.; Makin, H. L. J.; Trafford, D. J. H. J. Chem. Soc., Perkin Trans. 1 1983, 2563. Nemoto, H.; Suzuki, K.; Tsubuki, M.; Minemura, K.; Fukumoto, K.; Kametani, T.; Furuyama, H. Tetrahedron 1983, 39, 1123. Fehr, C. Helv. Chim. Acta 1983, 66, 2519. Hanessian, S.; Ugolini, A.; Dube, D.; Hodges, P. J.; Andre, C. J. Am. Chem. Soc. 1985, 108, 2776.
18. 9. Marko, I. E.; Murphy, F.; Dolan, S. Tetrahedron Lett. 1996, 37, 2089. This article also presents a nice solution to the reductive elimination problems associated with trisubstituted olefin synthesis using the metallated sulfone-ketone addition strategy (also see reference 14).
19. 10. For an article that describes trapping of lithiated sulfone-ketone adducts with methanesulfonyl chloride and subsequent conversion of the adducts to trisubstituted olefins see: Hsiao, C.-N.; Shechter, H. Tetrahedron Lett. 1982, 23, 1963.
20. 11. Guthrie, A. E.; Semple, J. E.; Joullie, M. M. J. Org. Chem. 1982, 47, 2369.
21. 12. Kocienski, P.; Todd, M. J. Chem. Soc., Perkin Trans. 1 1983, 1777.
22. 13. It has been reported that DME is useful in other reactions complicated by proton transfers: House, H. O. Rec. Chem. Prog. 1967, 28, 99.
23. 14. For recent advances regarding the use of samarium iodide in the second step of the Julia-Lythgoe olefination Kende, A. S.; Mendoza, J. S. Tetrahedron Lett. 1990, 31, 7105. Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Synlett 1994, 859. Keck, G. E.; Savin, K. A.; Weglarz, M. A. J. Org. Chem. 1995, 60, 3194 (also see reference 9).
24. 14. For recent advances regarding the use of samarium iodide in the second step of the Julia-Lythgoe olefination Kende, A. S.; Mendoza, J. S. Tetrahedron Lett. 1990, 31, 7105. Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Synlett 1994, 859. Keck, G. E.; Savin, K. A.; Weglarz, M. A. J. Org. Chem. 1995, 60, 3194 (also see reference 9).
25. 14. For recent advances regarding the use of samarium iodide in the second step of the Julia-Lythgoe olefination Kende, A. S.; Mendoza, J. S. Tetrahedron Lett. 1990, 31, 7105. Ihara, M.; Suzuki, S.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. Synlett 1994, 859. Keck, G. E.; Savin, K. A.; Weglarz, M. A. J. Org. Chem. 1995, 60, 3194 (also see reference 9).