Synthesis and Synthetic Utilization of α-Functionalized Vinylphosphonates Bearing β-Oxy or β-Thio Substituents

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6239-6246

  Kouno, Ryoji ^a   Okauchi, Tatsuo ^a   Nakamura, Mitsuharu ^a   Ichikawa, Junji ^a   Minami, Toru ^a  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000134602     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980467g     Document Type: Article

References (42)

1. For a review on synthetic uses of vinylphosphonates, see, (a) Minami, T.; Motoyoshiya, J. Synthesis 1992, 333. For biological uses, see, for example: (b) Kawamoto, A. P.; Campbell, M. M. J. Chem. Soc., Perkin Trans. 1 1997, 1249. Gao, J.; Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61, 9538.
2. For a review on synthetic uses of vinylphosphonates, see, (a) Minami, T.; Motoyoshiya, J. Synthesis 1992, 333. For biological uses, see, for example: (b) Kawamoto, A. P.; Campbell, M. M. J. Chem. Soc., Perkin Trans. 1 1997, 1249. Gao, J.; Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61, 9538.
3. For a review on synthetic uses of vinylphosphonates, see, (a) Minami, T.; Motoyoshiya, J. Synthesis 1992, 333. For biological uses, see, for example: (b) Kawamoto, A. P.; Campbell, M. M. J. Chem. Soc., Perkin Trans. 1 1997, 1249. Gao, J.; Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61, 9538.
4. For the synthesis and synthetic application of phosphonoketene dithioacetals, see: Minami, T.; Okauchi, T.; Matsuki, H.; Nakamura, M.; Ichikawa, J.; Ishida, M. J. Org. Chem. 1996, 61, 8132.
5. β-Alkyl-α-phosphonio- or phosphonovinyl anion easily isomerizes to the corresponding allyl anion. See: (a) Minami, T.; Shikita, S.; So, S.; Nakayama, M.; Yamamoto, I. J. Org. Chem. 1988, 53, 2937. (b) Kiddle, J. J.; Babler, J. H. J. Org. Chem. 1993, 58, 3572.
6. β-Alkyl-α-phosphonio- or phosphonovinyl anion easily isomerizes to the corresponding allyl anion. See: (a) Minami, T.; Shikita, S.; So, S.; Nakayama, M.; Yamamoto, I. J. Org. Chem. 1988, 53, 2937. (b) Kiddle, J. J.; Babler, J. H. J. Org. Chem. 1993, 58, 3572.
7. For the synthesis and synthetic application of α-phosphonoallenyl anion, see: (a) Macomber, R. S.; Hemling, T. C. J. Am. Chem. Soc. 1986, 108, 343. For β-aryl-α-phosphonovinyl anion, see: (b) Mimouni, N.; About-Jaudet, E.; Collignon, N.; Savignac, Ph. Phosphorus, Sulfur Silicon 1993, 75, 99.
8. For the synthesis and synthetic application of α-phosphonoallenyl anion, see: (a) Macomber, R. S.; Hemling, T. C. J. Am. Chem. Soc. 1986, 108, 343. For β-aryl-α-phosphonovinyl anion, see: (b) Mimouni, N.; About-Jaudet, E.; Collignon, N.; Savignac, Ph. Phosphorus, Sulfur Silicon 1993, 75, 99.
9. A related 1-lithio ketene dithioacetal has been reported to be generated by halogen/Li exchange of the corresponding bromoketene dithioacetal with t-BuLi at much lower temperature (at -120 °C), see: Chamberlin, A. R.; Nguyen, H. J. Org. Chem. 1986, 51, 940.
10. 1,2-Migration of the ethylthio group has been found to take place when acyclic dithioacetal 1b is added to a LTMP solution. See ref 2.
11. For the addition of phosphorus dithio acid to le, see: Kutyrev, G. A.; Kashina, N. V.; Ishmaeva, E. A.; Cherkasov, R. A.; Pudovic, A. N. Zh. Obshch. Khim. 1977, 47, 2460; Chem. Abstr. 1978, 88, 445.
12. For the addition of phosphorus dithio acid to le, see: Kutyrev, G. A.; Kashina, N. V.; Ishmaeva, E. A.; Cherkasov, R. A.; Pudovic, A. N. Zh. Obshch. Khim. 1977, 47, 2460; Chem. Abstr. 1978, 88, 445.
13. For the preparation of (Z)-2-(ethoxy)vinyllithium via halogen/ metal exchange between (Z)-2-(ethoxy)vinyl bromide and butyllithium, and reaction with carbonyl compounds, see: Lau, K. S. Y.; Schlosser, M. J. Org. Chem. 1978, 43, 1595.
14. 1H NMR parameters in substituted vinylphosphonates, see: (a) Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697 and references therein, (b) Galvez-Ruano, E.; Bellanato, J.; Fernandez-Ibanez, M.; Sainz-Diaz, C. I.; Arias-Perez, M. S. J. Mol. Struct. 1986, 142, 397. (c) Williamson, M. P.; Castellano, S.; Griffin, C. E. J. Phys. Chem. 1968, 72, 175. Also see ref 2.
15. 1H NMR parameters in substituted vinylphosphonates, see: (a) Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697 and references therein, (b) Galvez-Ruano, E.; Bellanato, J.; Fernandez-Ibanez, M.; Sainz-Diaz, C. I.; Arias-Perez, M. S. J. Mol. Struct. 1986, 142, 397. (c) Williamson, M. P.; Castellano, S.; Griffin, C. E. J. Phys. Chem. 1968, 72, 175. Also see ref 2.
16. 1H NMR parameters in substituted vinylphosphonates, see: (a) Xu, Y.; Flavin, M. T.; Xu, Z.-Q. J. Org. Chem. 1996, 61, 7697 and references therein, (b) Galvez-Ruano, E.; Bellanato, J.; Fernandez-Ibanez, M.; Sainz-Diaz, C. I.; Arias-Perez, M. S. J. Mol. Struct. 1986, 142, 397. (c) Williamson, M. P.; Castellano, S.; Griffin, C. E. J. Phys. Chem. 1968, 72, 175. Also see ref 2.
17. 3Si: (b) Grobel, B.-Th.; Seebach, D. Chem. Ber. 1977. 110, 867. For RO (c) see ref 8. For RS, see: (d) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. For a review of synthesis and synthetic application of α-seleno and α-telluro vinyl carbanions, see: (e) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410.
18. 3Si: (b) Grobel, B.-Th.; Seebach, D. Chem. Ber. 1977. 110, 867. For RO (c) see ref 8. For RS, see: (d) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. For a review of synthesis and synthetic application of α-seleno and α-telluro vinyl carbanions, see: (e) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410.
19. 3Si: (b) Grobel, B.-Th.; Seebach, D. Chem. Ber. 1977. 110, 867. For RO (c) see ref 8. For RS, see: (d) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. For a review of synthesis and synthetic application of α-seleno and α-telluro vinyl carbanions, see: (e) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410.
20. 3Si: (b) Grobel, B.-Th.; Seebach, D. Chem. Ber. 1977. 110, 867. For RO (c) see ref 8. For RS, see: (d) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. For a review of synthesis and synthetic application of α-seleno and α-telluro vinyl carbanions, see: (e) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410.
21. 3Si: (b) Grobel, B.-Th.; Seebach, D. Chem. Ber. 1977. 110, 867. For RO (c) see ref 8. For RS, see: (d) Takeda, T.; Furukawa, H.; Fujimori, M.; Suzuki, K.; Fujiwara, T. Bull. Chem. Soc. Jpn. 1984, 57, 1863. For a review of synthesis and synthetic application of α-seleno and α-telluro vinyl carbanions, see: (e) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1982, 21, 410.
22. Compound 18 was alternatively produced by direct acylataon of the vinyl carbanion, generated from la and LTMP m THF at -78 °C, with benzoyl chloride (2.0 equiv) in rather low yield (43%).
23. See, for examples: (a) Lambert, J. B. Tetrahedron 1990, 46, 2677. (b) Jarview, A. W. P. Organomet. Chem. Rev., Sect. A 1970, 6, 153. Colvin, W. E. Silicon in Organic Synthesis- Butterworth: London, 1981; Chapter 3.
24. See, for examples: (a) Lambert, J. B. Tetrahedron 1990, 46, 2677. (b) Jarview, A. W. P. Organomet. Chem. Rev., Sect. A 1970, 6, 153. Colvin, W. E. Silicon in Organic Synthesis- Butterworth: London, 1981; Chapter 3.
25. See, for examples: (a) Lambert, J. B. Tetrahedron 1990, 46, 2677. (b) Jarview, A. W. P. Organomet. Chem. Rev., Sect. A 1970, 6, 153. Colvin, W. E. Silicon in Organic Synthesis- Butterworth: London, 1981; Chapter 3.
26. See, for example; Price, C. C.; Oae, S. Sulfur Bonding- The Ronald Press Company: New York, 1962; Chapter 2.
27. A direct acylation of the α-carbanion from 1c with benzoyl chloride in THF at -78 °C were unsuccessful to give the compound in, since the product 21 underwent the Michael addition of the a-carbanion.
28. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Mitchell, T. N. Synthesis 1992, 803.
29. For reviews, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Mitchell, T. N. Synthesis 1992, 803.
30. For the effect of the Cu(I) salt cocatalyst on Stille cross-coupling reactions, see: Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359.
31. 2 (1.2 equiv) in THF at -78 °C to room temperature.
32. A direct synthesis of 20 by the reaction of an α-carbanion of β-(ethylthio)vinylphosphonate with chlorotrimethylsilane cannot be achieved, since treatment of the vinylphosphonate with LDA generates a β-carbanion, but not the α-carbanion. See ref 2.
33. For an alternative synthesis of 28, see: Hong, S.; Chang, K.; Ku, B.; Oh, D. Y. Tetrahedron Lett. 1989, 30, 3307.
34. For the cyclization of ketene dithioacetals to thiopyrazoles, see: (a) Taylor, E. C.; Purdum, W. R. Heterocycles 1977, 6, 1865. (b) Singh, G.; Deb, B.; Ila, H.; Junjappa, H. Synthesis 1987, 286.
35. For the cyclization of ketene dithioacetals to thiopyrazoles, see: (a) Taylor, E. C.; Purdum, W. R. Heterocycles 1977, 6, 1865. (b) Singh, G.; Deb, B.; Ila, H.; Junjappa, H. Synthesis 1987, 286.
36. For an alternative synthesis of 38, see: Aboujaoude, E. E.; Collignon, N.; Savignac, P. Tetrahedron 1985, 41, 427.
37. It is well-known that oximes undergo intramolecular Michael addition to electronegative olefins to give cyclic nitrones, see, for example; Minami, T.; Isonaka, T.; Okada, Y.; Ichikawa, J. J. Org. Chem. 1993, 58, 7009 and references therein. The spectral data of 40 were consistent with the structure described for eq 9 (see Experimental Section).
38. See, for examples, (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387.
39. See, for examples, (a) Danishefsky, S. J.; Shair, M. D. J. Org. Chem. 1996, 61, 16. (b) Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387.
40. Ishida, N.; Miyazaki, K.; Kumagai, K.; Rikimaru, M. J. Antibiol. 1965, 18, 68.
41. For palladium-mediated cross-coupling reactions between alkenyl halides and terminal alkynes, see, for example; Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 50, 4467.
42. Sonogashira, K. Comprehensive Organic Svnthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, Chapter 2.4, p 521.