Reaction of titanate-type aldehyde enolate with ketones to provide 3- hydroxyaldehydes [10]

Journal of the American Chemical Society

Volumn 121, Issue 40, 1999, Pages 9465-9466

  Yachi, Kentaro ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYALDEHYDE DERIVATIVE; ALDEHYDE DERIVATIVE; KETONE DERIVATIVE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0033552258     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9921975     Document Type: Letter

References (38)

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13. 3). The formation energy of the latter is -10.455 kcal/mol, whereas that of the former is 21.155 kcal/mol.
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15. (b) Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986.
16. For preparation of lithium enolate of aldehyde, see: Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066.
17. Some reactions involving titanium ate-complex reagents have been reported: (a) Reetz, M. T.; Peter, T. Tetrahedron Lett. 1981, 22, 4691. (b) Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259. (c) Reetz, M. T.; Westermann, J.: Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421. (d) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441.
18. Some reactions involving titanium ate-complex reagents have been reported: (a) Reetz, M. T.; Peter, T. Tetrahedron Lett. 1981, 22, 4691. (b) Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259. (c) Reetz, M. T.; Westermann, J.: Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421. (d) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441.
19. Some reactions involving titanium ate-complex reagents have been reported: (a) Reetz, M. T.; Peter, T. Tetrahedron Lett. 1981, 22, 4691. (b) Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259. (c) Reetz, M. T.; Westermann, J.: Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421. (d) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441.
20. Some reactions involving titanium ate-complex reagents have been reported: (a) Reetz, M. T.; Peter, T. Tetrahedron Lett. 1981, 22, 4691. (b) Reetz, M. T.; Wenderoth, B. Tetrahedron Lett. 1982, 23, 5259. (c) Reetz, M. T.; Westermann, J.: Steinbach, R.; Wenderoth, B.; Peter, R.; Ostarek, R.; Maus, S. Chem. Ber. 1985, 118, 1421. (d) Reetz, M. T.; Steinbach, R.; Westermann, J.; Peter, R.; Wenderoth, B. Chem. Ber. 1985, 118, 1441.
21. For aldol-type reactions involving titanium enolate, see: (a) Nakamura, E.; Shimada, J.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3341. (b) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343. (c) Harrison, C. R. Tetrahedron Lett. 1987, 28, 4134. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211. (e) Morris, J.; Wishka, D. G.; Luke, G. P.; Judge, T. M.; Gammill, R. B. Tetrahedron 1997, 53 11211. (f) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883. (g) Toshida, Y.; Hayashi, R.; Sumihara, H.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 8727. (h) Baker, R. K.; Rupprecht, K. M.; Armistead, D. M.; Boger, J.; Frankshun, R. A.; Hodges, P. J.; Hoogsteen, K.; Pisano, J. M.; Witzel, B. E. Tetrahedron Lett. 1998, 39, 229. (i) Mahrwald, R.; Gündogan, B. J. Am. Chem. Soc. 1998, 120, 413.
22. For aldol-type reactions involving titanium enolate, see: (a) Nakamura, E.; Shimada, J.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3341. (b) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343. (c) Harrison, C. R. Tetrahedron Lett. 1987, 28, 4134. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211. (e) Morris, J.; Wishka, D. G.; Luke, G. P.; Judge, T. M.; Gammill, R. B. Tetrahedron 1997, 53 11211. (f) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883. (g) Toshida, Y.; Hayashi, R.; Sumihara, H.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 8727. (h) Baker, R. K.; Rupprecht, K. M.; Armistead, D. M.; Boger, J.; Frankshun, R. A.; Hodges, P. J.; Hoogsteen, K.; Pisano, J. M.; Witzel, B. E. Tetrahedron Lett. 1998, 39, 229. (i) Mahrwald, R.; Gündogan, B. J. Am. Chem. Soc. 1998, 120, 413.
23. For aldol-type reactions involving titanium enolate, see: (a) Nakamura, E.; Shimada, J.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3341. (b) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343. (c) Harrison, C. R. Tetrahedron Lett. 1987, 28, 4134. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211. (e) Morris, J.; Wishka, D. G.; Luke, G. P.; Judge, T. M.; Gammill, R. B. Tetrahedron 1997, 53 11211. (f) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883. (g) Toshida, Y.; Hayashi, R.; Sumihara, H.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 8727. (h) Baker, R. K.; Rupprecht, K. M.; Armistead, D. M.; Boger, J.; Frankshun, R. A.; Hodges, P. J.; Hoogsteen, K.; Pisano, J. M.; Witzel, B. E. Tetrahedron Lett. 1998, 39, 229. (i) Mahrwald, R.; Gündogan, B. J. Am. Chem. Soc. 1998, 120, 413.
24. For aldol-type reactions involving titanium enolate, see: (a) Nakamura, E.; Shimada, J.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3341. (b) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343. (c) Harrison, C. R. Tetrahedron Lett. 1987, 28, 4134. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211. (e) Morris, J.; Wishka, D. G.; Luke, G. P.; Judge, T. M.; Gammill, R. B. Tetrahedron 1997, 53 11211. (f) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883. (g) Toshida, Y.; Hayashi, R.; Sumihara, H.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 8727. (h) Baker, R. K.; Rupprecht, K. M.; Armistead, D. M.; Boger, J.; Frankshun, R. A.; Hodges, P. J.; Hoogsteen, K.; Pisano, J. M.; Witzel, B. E. Tetrahedron Lett. 1998, 39, 229. (i) Mahrwald, R.; Gündogan, B. J. Am. Chem. Soc. 1998, 120, 413.
25. For aldol-type reactions involving titanium enolate, see: (a) Nakamura, E.; Shimada, J.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3341. (b) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343. (c) Harrison, C. R. Tetrahedron Lett. 1987, 28, 4134. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211. (e) Morris, J.; Wishka, D. G.; Luke, G. P.; Judge, T. M.; Gammill, R. B. Tetrahedron 1997, 53 11211. (f) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883. (g) Toshida, Y.; Hayashi, R.; Sumihara, H.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 8727. (h) Baker, R. K.; Rupprecht, K. M.; Armistead, D. M.; Boger, J.; Frankshun, R. A.; Hodges, P. J.; Hoogsteen, K.; Pisano, J. M.; Witzel, B. E. Tetrahedron Lett. 1998, 39, 229. (i) Mahrwald, R.; Gündogan, B. J. Am. Chem. Soc. 1998, 120, 413.
26. For aldol-type reactions involving titanium enolate, see: (a) Nakamura, E.; Shimada, J.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3341. (b) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343. (c) Harrison, C. R. Tetrahedron Lett. 1987, 28, 4134. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211. (e) Morris, J.; Wishka, D. G.; Luke, G. P.; Judge, T. M.; Gammill, R. B. Tetrahedron 1997, 53 11211. (f) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883. (g) Toshida, Y.; Hayashi, R.; Sumihara, H.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 8727. (h) Baker, R. K.; Rupprecht, K. M.; Armistead, D. M.; Boger, J.; Frankshun, R. A.; Hodges, P. J.; Hoogsteen, K.; Pisano, J. M.; Witzel, B. E. Tetrahedron Lett. 1998, 39, 229. (i) Mahrwald, R.; Gündogan, B. J. Am. Chem. Soc. 1998, 120, 413.
27. For aldol-type reactions involving titanium enolate, see: (a) Nakamura, E.; Shimada, J.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3341. (b) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343. (c) Harrison, C. R. Tetrahedron Lett. 1987, 28, 4134. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211. (e) Morris, J.; Wishka, D. G.; Luke, G. P.; Judge, T. M.; Gammill, R. B. Tetrahedron 1997, 53 11211. (f) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883. (g) Toshida, Y.; Hayashi, R.; Sumihara, H.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 8727. (h) Baker, R. K.; Rupprecht, K. M.; Armistead, D. M.; Boger, J.; Frankshun, R. A.; Hodges, P. J.; Hoogsteen, K.; Pisano, J. M.; Witzel, B. E. Tetrahedron Lett. 1998, 39, 229. (i) Mahrwald, R.; Gündogan, B. J. Am. Chem. Soc. 1998, 120, 413.
28. For aldol-type reactions involving titanium enolate, see: (a) Nakamura, E.; Shimada, J.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3341. (b) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343. (c) Harrison, C. R. Tetrahedron Lett. 1987, 28, 4134. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211. (e) Morris, J.; Wishka, D. G.; Luke, G. P.; Judge, T. M.; Gammill, R. B. Tetrahedron 1997, 53 11211. (f) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883. (g) Toshida, Y.; Hayashi, R.; Sumihara, H.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 8727. (h) Baker, R. K.; Rupprecht, K. M.; Armistead, D. M.; Boger, J.; Frankshun, R. A.; Hodges, P. J.; Hoogsteen, K.; Pisano, J. M.; Witzel, B. E. Tetrahedron Lett. 1998, 39, 229. (i) Mahrwald, R.; Gündogan, B. J. Am. Chem. Soc. 1998, 120, 413.
29. For aldol-type reactions involving titanium enolate, see: (a) Nakamura, E.; Shimada, J.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3341. (b) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343. (c) Harrison, C. R. Tetrahedron Lett. 1987, 28, 4134. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211. (e) Morris, J.; Wishka, D. G.; Luke, G. P.; Judge, T. M.; Gammill, R. B. Tetrahedron 1997, 53 11211. (f) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883. (g) Toshida, Y.; Hayashi, R.; Sumihara, H.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 8727. (h) Baker, R. K.; Rupprecht, K. M.; Armistead, D. M.; Boger, J.; Frankshun, R. A.; Hodges, P. J.; Hoogsteen, K.; Pisano, J. M.; Witzel, B. E. Tetrahedron Lett. 1998, 39, 229. (i) Mahrwald, R.; Gündogan, B. J. Am. Chem. Soc. 1998, 120, 413.
30. For aldol-type reactions involving titanium enolate, see: (a) Nakamura, E.; Shimada, J.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3341. (b) Nakamura, E.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3343. (c) Harrison, C. R. Tetrahedron Lett. 1987, 28, 4134. (d) Siegel, C.; Thornton, E. R. J. Am. Chem. Soc. 1989, 111, 5722. Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211. (e) Morris, J.; Wishka, D. G.; Luke, G. P.; Judge, T. M.; Gammill, R. B. Tetrahedron 1997, 53 11211. (f) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883. (g) Toshida, Y.; Hayashi, R.; Sumihara, H.; Tanabe, Y. Tetrahedron Lett. 1997, 38, 8727. (h) Baker, R. K.; Rupprecht, K. M.; Armistead, D. M.; Boger, J.; Frankshun, R. A.; Hodges, P. J.; Hoogsteen, K.; Pisano, J. M.; Witzel, B. E. Tetrahedron Lett. 1998, 39, 229. (i) Mahrwald, R.; Gündogan, B. J. Am. Chem. Soc. 1998, 120, 413.
31. 3SiCl afforded the starting silyl enolate (Z)-4 (Z/E = >99/<1) in quantitative yield. From this result, no isomerization of enolates 5 and 6 occurred during the transmetalation step.
32. 4 was not effective, and 7a was obtained in reduced yield (47%, synlanti = 70/30) upon treatment with 2-methylpropanal.
33. The reaction of titanate enolate prepared from 2-ethyl-1-trimethyl-siloxy-1-butene with ketones provided no aldol adduct.
34. 4, no trace of 10 could be observed in the reaction mixture, and complex products were formed.
35. Reetz, M. T. Top. Curr. Chem. 1982, 106, 1. See also ref 7c.
36. This stereochemical outcome might indicate that this reaction proceeds under thermodynamic control.
37. Imwinkelried, R.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1985, 24, 765.
38. For temporary protection by aminotitanium complexes, see; Reetz, M. T.; Peter, R. J. Chem. Soc., Chem. Commun. 1983, 406. See also refs 7b and 7c.