Dependence of the reactivities of titanium enolates on how they are generated: Diastereoselective coupling of phenylacetic acid esters using titanium tetrachloride

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2809-2812

  Matsumura, Yoshihiro ^a   Nishimura, Maiko ^a   Hiu, Hiroyuki ^a   Watanabe, Mitsuaki ^a   Kise, Naoki ^b  

^a NAGASAKI UNIVERSITY   (Japan)

^b TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000323266     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952204h     Document Type: Article

References (33)

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15. Although 4-isopropyl-3-(phenylacetyl)-2-oxazolidone was coupled by method iii, it gave a complex mixture of products by method i; see ref 4g.
16. There are a variety of methods for the oxidative homocoupling of phenylacetic acid derivatives. (i) Through enolate anions: (a) Kofron, W. G.; Hauser, C. R. J. Org. Chem. 1970, 35, 2085. (b) Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 4605. (c) Tokuda, M.; Shigei, T.; Itoh, M. Chem. Lett. 1975, 621. (ii) Through carboxylic dianions (d) Belletire, J. L.; Spletzer, E. G.; Pinhas, A. R. Tetrahedron Lett. 1984, 25, 5969. (e) Renaud, P. Fox, M. A. J. Org. Chem. 1988, 53, 3745. For the oxidative homocoupling of other esters (f) Chung, S. K.; Dunn, L. B., Jr. J. Org. Chem. 1983, 48, 1125. (g) Belletire, J. L.; Fremont, S. L. Tetrahedron Lett. 1986, 27, 127. (h) Belletire, J. L.; Fry, D. F. J. Org. Chem 1987, 52, 2549. (i) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457. (j) Langer, T.; Illich, M.; Helmachen, G. Tetrahedron Lett. 1995, 36, 4409.
17. There are a variety of methods for the oxidative homocoupling of phenylacetic acid derivatives. (i) Through enolate anions: (a) Kofron, W. G.; Hauser, C. R. J. Org. Chem. 1970, 35, 2085. (b) Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 4605. (c) Tokuda, M.; Shigei, T.; Itoh, M. Chem. Lett. 1975, 621. (ii) Through carboxylic dianions (d) Belletire, J. L.; Spletzer, E. G.; Pinhas, A. R. Tetrahedron Lett. 1984, 25, 5969. (e) Renaud, P. Fox, M. A. J. Org. Chem. 1988, 53, 3745. For the oxidative homocoupling of other esters (f) Chung, S. K.; Dunn, L. B., Jr. J. Org. Chem. 1983, 48, 1125. (g) Belletire, J. L.; Fremont, S. L. Tetrahedron Lett. 1986, 27, 127. (h) Belletire, J. L.; Fry, D. F. J. Org. Chem 1987, 52, 2549. (i) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457. (j) Langer, T.; Illich, M.; Helmachen, G. Tetrahedron Lett. 1995, 36, 4409.
18. There are a variety of methods for the oxidative homocoupling of phenylacetic acid derivatives. (i) Through enolate anions: (a) Kofron, W. G.; Hauser, C. R. J. Org. Chem. 1970, 35, 2085. (b) Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 4605. (c) Tokuda, M.; Shigei, T.; Itoh, M. Chem. Lett. 1975, 621. (ii) Through carboxylic dianions (d) Belletire, J. L.; Spletzer, E. G.; Pinhas, A. R. Tetrahedron Lett. 1984, 25, 5969. (e) Renaud, P. Fox, M. A. J. Org. Chem. 1988, 53, 3745. For the oxidative homocoupling of other esters (f) Chung, S. K.; Dunn, L. B., Jr. J. Org. Chem. 1983, 48, 1125. (g) Belletire, J. L.; Fremont, S. L. Tetrahedron Lett. 1986, 27, 127. (h) Belletire, J. L.; Fry, D. F. J. Org. Chem 1987, 52, 2549. (i) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457. (j) Langer, T.; Illich, M.; Helmachen, G. Tetrahedron Lett. 1995, 36, 4409.
19. There are a variety of methods for the oxidative homocoupling of phenylacetic acid derivatives. (i) Through enolate anions: (a) Kofron, W. G.; Hauser, C. R. J. Org. Chem. 1970, 35, 2085. (b) Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 4605. (c) Tokuda, M.; Shigei, T.; Itoh, M. Chem. Lett. 1975, 621. (ii) Through carboxylic dianions (d) Belletire, J. L.; Spletzer, E. G.; Pinhas, A. R. Tetrahedron Lett. 1984, 25, 5969. (e) Renaud, P. Fox, M. A. J. Org. Chem. 1988, 53, 3745. For the oxidative homocoupling of other esters (f) Chung, S. K.; Dunn, L. B., Jr. J. Org. Chem. 1983, 48, 1125. (g) Belletire, J. L.; Fremont, S. L. Tetrahedron Lett. 1986, 27, 127. (h) Belletire, J. L.; Fry, D. F. J. Org. Chem 1987, 52, 2549. (i) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457. (j) Langer, T.; Illich, M.; Helmachen, G. Tetrahedron Lett. 1995, 36, 4409.
20. There are a variety of methods for the oxidative homocoupling of phenylacetic acid derivatives. (i) Through enolate anions: (a) Kofron, W. G.; Hauser, C. R. J. Org. Chem. 1970, 35, 2085. (b) Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 4605. (c) Tokuda, M.; Shigei, T.; Itoh, M. Chem. Lett. 1975, 621. (ii) Through carboxylic dianions (d) Belletire, J. L.; Spletzer, E. G.; Pinhas, A. R. Tetrahedron Lett. 1984, 25, 5969. (e) Renaud, P. Fox, M. A. J. Org. Chem. 1988, 53, 3745. For the oxidative homocoupling of other esters (f) Chung, S. K.; Dunn, L. B., Jr. J. Org. Chem. 1983, 48, 1125. (g) Belletire, J. L.; Fremont, S. L. Tetrahedron Lett. 1986, 27, 127. (h) Belletire, J. L.; Fry, D. F. J. Org. Chem 1987, 52, 2549. (i) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457. (j) Langer, T.; Illich, M.; Helmachen, G. Tetrahedron Lett. 1995, 36, 4409.
21. There are a variety of methods for the oxidative homocoupling of phenylacetic acid derivatives. (i) Through enolate anions: (a) Kofron, W. G.; Hauser, C. R. J. Org. Chem. 1970, 35, 2085. (b) Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 4605. (c) Tokuda, M.; Shigei, T.; Itoh, M. Chem. Lett. 1975, 621. (ii) Through carboxylic dianions (d) Belletire, J. L.; Spletzer, E. G.; Pinhas, A. R. Tetrahedron Lett. 1984, 25, 5969. (e) Renaud, P. Fox, M. A. J. Org. Chem. 1988, 53, 3745. For the oxidative homocoupling of other esters (f) Chung, S. K.; Dunn, L. B., Jr. J. Org. Chem. 1983, 48, 1125. (g) Belletire, J. L.; Fremont, S. L. Tetrahedron Lett. 1986, 27, 127. (h) Belletire, J. L.; Fry, D. F. J. Org. Chem 1987, 52, 2549. (i) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457. (j) Langer, T.; Illich, M.; Helmachen, G. Tetrahedron Lett. 1995, 36, 4409.
22. There are a variety of methods for the oxidative homocoupling of phenylacetic acid derivatives. (i) Through enolate anions: (a) Kofron, W. G.; Hauser, C. R. J. Org. Chem. 1970, 35, 2085. (b) Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 4605. (c) Tokuda, M.; Shigei, T.; Itoh, M. Chem. Lett. 1975, 621. (ii) Through carboxylic dianions (d) Belletire, J. L.; Spletzer, E. G.; Pinhas, A. R. Tetrahedron Lett. 1984, 25, 5969. (e) Renaud, P. Fox, M. A. J. Org. Chem. 1988, 53, 3745. For the oxidative homocoupling of other esters (f) Chung, S. K.; Dunn, L. B., Jr. J. Org. Chem. 1983, 48, 1125. (g) Belletire, J. L.; Fremont, S. L. Tetrahedron Lett. 1986, 27, 127. (h) Belletire, J. L.; Fry, D. F. J. Org. Chem 1987, 52, 2549. (i) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457. (j) Langer, T.; Illich, M.; Helmachen, G. Tetrahedron Lett. 1995, 36, 4409.
23. There are a variety of methods for the oxidative homocoupling of phenylacetic acid derivatives. (i) Through enolate anions: (a) Kofron, W. G.; Hauser, C. R. J. Org. Chem. 1970, 35, 2085. (b) Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 4605. (c) Tokuda, M.; Shigei, T.; Itoh, M. Chem. Lett. 1975, 621. (ii) Through carboxylic dianions (d) Belletire, J. L.; Spletzer, E. G.; Pinhas, A. R. Tetrahedron Lett. 1984, 25, 5969. (e) Renaud, P. Fox, M. A. J. Org. Chem. 1988, 53, 3745. For the oxidative homocoupling of other esters (f) Chung, S. K.; Dunn, L. B., Jr. J. Org. Chem. 1983, 48, 1125. (g) Belletire, J. L.; Fremont, S. L. Tetrahedron Lett. 1986, 27, 127. (h) Belletire, J. L.; Fry, D. F. J. Org. Chem 1987, 52, 2549. (i) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457. (j) Langer, T.; Illich, M.; Helmachen, G. Tetrahedron Lett. 1995, 36, 4409.
24. There are a variety of methods for the oxidative homocoupling of phenylacetic acid derivatives. (i) Through enolate anions: (a) Kofron, W. G.; Hauser, C. R. J. Org. Chem. 1970, 35, 2085. (b) Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 4605. (c) Tokuda, M.; Shigei, T.; Itoh, M. Chem. Lett. 1975, 621. (ii) Through carboxylic dianions (d) Belletire, J. L.; Spletzer, E. G.; Pinhas, A. R. Tetrahedron Lett. 1984, 25, 5969. (e) Renaud, P. Fox, M. A. J. Org. Chem. 1988, 53, 3745. For the oxidative homocoupling of other esters (f) Chung, S. K.; Dunn, L. B., Jr. J. Org. Chem. 1983, 48, 1125. (g) Belletire, J. L.; Fremont, S. L. Tetrahedron Lett. 1986, 27, 127. (h) Belletire, J. L.; Fry, D. F. J. Org. Chem 1987, 52, 2549. (i) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457. (j) Langer, T.; Illich, M.; Helmachen, G. Tetrahedron Lett. 1995, 36, 4409.
25. There are a variety of methods for the oxidative homocoupling of phenylacetic acid derivatives. (i) Through enolate anions: (a) Kofron, W. G.; Hauser, C. R. J. Org. Chem. 1970, 35, 2085. (b) Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 4605. (c) Tokuda, M.; Shigei, T.; Itoh, M. Chem. Lett. 1975, 621. (ii) Through carboxylic dianions (d) Belletire, J. L.; Spletzer, E. G.; Pinhas, A. R. Tetrahedron Lett. 1984, 25, 5969. (e) Renaud, P. Fox, M. A. J. Org. Chem. 1988, 53, 3745. For the oxidative homocoupling of other esters (f) Chung, S. K.; Dunn, L. B., Jr. J. Org. Chem. 1983, 48, 1125. (g) Belletire, J. L.; Fremont, S. L. Tetrahedron Lett. 1986, 27, 127. (h) Belletire, J. L.; Fry, D. F. J. Org. Chem 1987, 52, 2549. (i) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457. (j) Langer, T.; Illich, M.; Helmachen, G. Tetrahedron Lett. 1995, 36, 4409.
26. Diisopropylethylamine and spartein also gave similar results.
27. The coupling also took place at -78 °C, but a longer reaction time was required (after 4.5 h, dl-6a/meso-6a = 95/5, 85% yiel).
28. 3.
29. We obtained a yield of 27%, while a yield of 76% was described in ref 3a.
30. de Luca, C.; Insei, A.; Rampazzo, L. J. Chem. Soc., Perkin Trans. 2, 1982, 1403.
31. The numbers in parentheses are in ref 2.
32. Cadogan, J. I. G.; Hey, D. H.; Ong, S H. J. Chem. Soc. 1965, 1939.
33. Wren, H.; Still, C. J. J. Chem. Soc 1915, 107, 444.