Expedient construction of multiple stereogenic centers in an acyclic system via the addition of aldehydes, ketones, and chiral imines to an enyne - Titanium alkoxide complex [13]

Journal of the American Chemical Society

Volumn 122, Issue 29, 2000, Pages 7138-7139

  Hamada, Takashi ^a   Mizojiri, Ryo ^a   Urabe, Hirokazu ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBONYL DERIVATIVE; IMINE; KETONE; TITANIUM DERIVATIVE;

CHEMICAL BOND; CHEMICAL REACTION; CHIRALITY; LETTER; OPTICAL ROTATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034718071     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001334r     Document Type: Letter

References (39)

1. Although there are numerous methods available for the stereoselective construction of two stereogenic centers, those for more than three in an asymmetric fashion are less common. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990. Trost, B. M.; Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 5. Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195-206. Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
2. Although there are numerous methods available for the stereoselective construction of two stereogenic centers, those for more than three in an asymmetric fashion are less common. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990. Trost, B. M.; Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 5. Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195-206. Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
3. Although there are numerous methods available for the stereoselective construction of two stereogenic centers, those for more than three in an asymmetric fashion are less common. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990. Trost, B. M.; Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 5. Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195-206. Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
4. Although there are numerous methods available for the stereoselective construction of two stereogenic centers, those for more than three in an asymmetric fashion are less common. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990. Trost, B. M.; Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 5. Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195-206. Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
5. Although there are numerous methods available for the stereoselective construction of two stereogenic centers, those for more than three in an asymmetric fashion are less common. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990. Trost, B. M.; Fleming, I., Eds. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 5. Bunce, R. A. Tetrahedron 1995, 51, 13103-13159. Parsons, P. J.; Penkett, C. S.; Shell, A. J. Chem. Rev. 1996, 96, 195-206. Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
6. For review on group 4 metal-acetylene and -olefin complexes, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
7. For review on group 4 metal-acetylene and -olefin complexes, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
8. For review on group 4 metal-acetylene and -olefin complexes, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
9. For review on group 4 metal-acetylene and -olefin complexes, see: Buchwald, S. L.; Nielsen, R. B. Chem. Rev. 1988, 88, 1047-1058. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124-130. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burlakov, V. V.; Rosenthal, U. Synlett 1996, 111-118. Negishi, E.; Takahashi, T. Bull. Chem. Soc. Jpn. 1998, 71, 755-769.
10. A few group 4 metal-conjugated enyne complexes were reported, but their unique synthetic utility has not been pursued. Stepnicka, P.; Gyepes, R.; Císarová, I.; Horácek, M.; Kubista, J.; Mach, K. Organometallics 1999, 18, 4869-4880. Takahashi, T.; Xi, Z.; Nishihara, Y.; Huo, S.; Kasai, K.; Aoyagi, K.; Denisov, V.; Negishi, E. Tetrahedron 1997, 53, 9123-9134.
11. A few group 4 metal-conjugated enyne complexes were reported, but their unique synthetic utility has not been pursued. Stepnicka, P.; Gyepes, R.; Císarová, I.; Horácek, M.; Kubista, J.; Mach, K. Organometallics 1999, 18, 4869-4880. Takahashi, T.; Xi, Z.; Nishihara, Y.; Huo, S.; Kasai, K.; Aoyagi, K.; Denisov, V.; Negishi, E. Tetrahedron 1997, 53, 9123-9134.
12. Cf. group 4 metal-acetylene complexes are known to add to aldehydes, ketones, or imines, but the reaction stops at the stage of mono-addition (see literature cited in references 2, 6, and 10). For the double addition to group 4 metal-olefin or -diene complexes, see: Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Fanwick, P. E.; Roth well, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641. Yasuda, H.; Tatsumi, K.; Nakamura, A. Acc. Chem. Res. 1985, 18, 120-126.
13. Cf. group 4 metal-acetylene complexes are known to add to aldehydes, ketones, or imines, but the reaction stops at the stage of mono-addition (see literature cited in references 2, 6, and 10). For the double addition to group 4 metal-olefin or -diene complexes, see: Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Fanwick, P. E.; Roth well, I. P. J. Am. Chem. Soc. 1997, 119, 8630-8641. Yasuda, H.; Tatsumi, K.; Nakamura, A. Acc. Chem. Res. 1985, 18, 120-126.
14. N2′ displacement of propargyl alcohol derivatives. Thus, the conversion of eq 1 should provide a different way to make such allenes.
15. N2′ displacement of propargyl alcohol derivatives. Thus, the conversion of eq 1 should provide a different way to make such allenes.
16. N2′ displacement of propargyl alcohol derivatives. Thus, the conversion of eq 1 should provide a different way to make such allenes.
17. N2′ displacement of propargyl alcohol derivatives. Thus, the conversion of eq 1 should provide a different way to make such allenes.
18. N2′ displacement of propargyl alcohol derivatives. Thus, the conversion of eq 1 should provide a different way to make such allenes.
19. N2′ displacement of propargyl alcohol derivatives. Thus, the conversion of eq 1 should provide a different way to make such allenes.
20. N2′ displacement of propargyl alcohol derivatives. Thus, the conversion of eq 1 should provide a different way to make such allenes.
21. N2′ displacement of propargyl alcohol derivatives. Thus, the conversion of eq 1 should provide a different way to make such allenes.
22. N2′ displacement of propargyl alcohol derivatives. Thus, the conversion of eq 1 should provide a different way to make such allenes.
23. N2′ displacement of propargyl alcohol derivatives. Thus, the conversion of eq 1 should provide a different way to make such allenes.
24. N2′ displacement of propargyl alcohol derivatives. Thus, the conversion of eq 1 should provide a different way to make such allenes.
25. N2′ displacement of propargyl alcohol derivatives. Thus, the conversion of eq 1 should provide a different way to make such allenes.
26. (a) Sato, F.; Urabe, H.; Okamoto, S. Pure Appl. Chem. 1999, 71, 1511-1519.
27. (b) Harada, K.; Urabe, H.; Sato, F. Tetrahedron Lett. 1995, 36, 3203-3206.
28. Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492-4493.
29. See Supporting Information.
30. Pivalaldehyde was chosen as the second aldehyde in order to discriminate between the two hydroxy groups in 18 for structural determination.
31. The addition to imines must be carried out in ether-THF(1:1) rather than ether (cf. Schemes 1 and 2); otherwise, a mixture of allenylamine and undesired dienylamine is produced. Unfortunately, (Z)-enyne complex 5 behaved like a simple acetylene-titanium complex to furnish only dienylamines. For the reaction of the simple acetylene complexes with imines, see: Gao, Y.; Harada, K.; Sato, F. Tetrahedron Lett. 1995, 36, 5913-5916.
32. Juaristi, E.; León-Romo, J. L., Reyes, A.; Escalante, J. Tetrahedron: Asymmetry 1999, 10, 2441-2495. Bloch, R. Chem. Rev. 1998, 98, 1407-1438. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. Gao, Y.; Sato, F. J. Org. Chem. 1995, 60, 8136-8137.
33. Juaristi, E.; León-Romo, J. L., Reyes, A.; Escalante, J. Tetrahedron: Asymmetry 1999, 10, 2441-2495. Bloch, R. Chem. Rev. 1998, 98, 1407-1438. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. Gao, Y.; Sato, F. J. Org. Chem. 1995, 60, 8136-8137.
34. Juaristi, E.; León-Romo, J. L., Reyes, A.; Escalante, J. Tetrahedron: Asymmetry 1999, 10, 2441-2495. Bloch, R. Chem. Rev. 1998, 98, 1407-1438. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. Gao, Y.; Sato, F. J. Org. Chem. 1995, 60, 8136-8137.
35. Juaristi, E.; León-Romo, J. L., Reyes, A.; Escalante, J. Tetrahedron: Asymmetry 1999, 10, 2441-2495. Bloch, R. Chem. Rev. 1998, 98, 1407-1438. Enders, D.; Reinhold: U. Tetrahedron: Asymmetry 1997, 8, 1895-1946. Gao, Y.; Sato, F. J. Org. Chem. 1995, 60, 8136-8137.
36. Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp 521-549.
37. For the reactions of organotitanium compounds, see: Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986. Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 139-172. Reetz, M. T. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, 1994; pp 195-282.
38. For the reactions of organotitanium compounds, see: Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986. Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 139-172. Reetz, M. T. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, 1994; pp 195-282.
39. For the reactions of organotitanium compounds, see: Reetz, M. T. Organotitanium Reagents in Organic Synthesis; Springer-Verlag: Berlin, 1986. Ferreri, C.; Palumbo, G.; Caputo, R. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, pp 139-172. Reetz, M. T. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, 1994; pp 195-282.