Highly anti-selective catalytic asymmetric aldol reactions [9]

Journal of the American Chemical Society

Volumn 122, Issue 22, 2000, Pages 5403-5404

  Ishitani, Haruro ^a   Yamashila, Yasuhiro ^a   Shimizu, Haruka ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE;

CATALYSIS; CATALYST; CHEMICAL REACTION; DIASTEREOISOMER; GAS CHROMATOGRAPHY; LETTER; LIGAND BINDING; MASS SPECTROMETRY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0034616874     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9943389     Document Type: Letter

References (43)

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11. Some catalytic asymmetric aldol reactions were performed at higher temperatures (-20 to 23°C): (a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (b) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837. (c) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Catalytic asymmetric aldol reactions in wet dimethylformamide were reported: (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
12. Some catalytic asymmetric aldol reactions were performed at higher temperatures (-20 to 23°C): (a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (b) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837. (c) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Catalytic asymmetric aldol reactions in wet dimethylformamide were reported: (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
13. Some catalytic asymmetric aldol reactions were performed at higher temperatures (-20 to 23°C): (a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (b) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837. (c) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Catalytic asymmetric aldol reactions in wet dimethylformamide were reported: (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
14. Some catalytic asymmetric aldol reactions were performed at higher temperatures (-20 to 23°C): (a) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (b) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837. (c) Keck, G. E.; Krishnamurthy, D. J. Am. Chem. Soc. 1995, 117, 2363. Catalytic asymmetric aldol reactions in wet dimethylformamide were reported: (d) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
15. Masamune et al. reported anti-selective catalytic asymmetric aldol reactions; however, the enantioselectivities of the anti-adducts were 60-82% ees. (a) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729. For other anti-selective catalytic asymmetric aldol reactions: (b) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (c) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (d) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982. (e) Evans, D. A.; MacMillan, W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Although high selectivities are obtained in some of these reactions, substrates are limited in all cases.
16. Masamune et al. reported anti-selective catalytic asymmetric aldol reactions; however, the enantioselectivities of the anti-adducts were 60-82% ees. (a) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729. For other anti-selective catalytic asymmetric aldol reactions: (b) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (c) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (d) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982. (e) Evans, D. A.; MacMillan, W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Although high selectivities are obtained in some of these reactions, substrates are limited in all cases.
17. Masamune et al. reported anti-selective catalytic asymmetric aldol reactions; however, the enantioselectivities of the anti-adducts were 60-82% ees. (a) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729. For other anti-selective catalytic asymmetric aldol reactions: (b) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (c) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (d) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982. (e) Evans, D. A.; MacMillan, W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Although high selectivities are obtained in some of these reactions, substrates are limited in all cases.
18. Masamune et al. reported anti-selective catalytic asymmetric aldol reactions; however, the enantioselectivities of the anti-adducts were 60-82% ees. (a) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729. For other anti-selective catalytic asymmetric aldol reactions: (b) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (c) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (d) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982. (e) Evans, D. A.; MacMillan, W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Although high selectivities are obtained in some of these reactions, substrates are limited in all cases.
19. Masamune et al. reported anti-selective catalytic asymmetric aldol reactions; however, the enantioselectivities of the anti-adducts were 60-82% ees. (a) Parmee, E. R.; Hong, Y.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729. For other anti-selective catalytic asymmetric aldol reactions: (b) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1994, 116, 4077. (c) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (d) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982. (e) Evans, D. A.; MacMillan, W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. Although high selectivities are obtained in some of these reactions, substrates are limited in all cases.
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28. For other examples of zirconium-based asymmetric catalysts: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (b) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (c) Yu, C.-M.; Yoon, S.-K.; Choi, H.-S.; Back, K. Chem. Commun. 1997, 763. (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262.
29. For other examples of zirconium-based asymmetric catalysts: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (b) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (c) Yu, C.-M.; Yoon, S.-K.; Choi, H.-S.; Back, K. Chem. Commun. 1997, 763. (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262.
30. For other examples of zirconium-based asymmetric catalysts: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (b) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (c) Yu, C.-M.; Yoon, S.-K.; Choi, H.-S.; Back, K. Chem. Commun. 1997, 763. (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262.
31. For other examples of zirconium-based asymmetric catalysts: (a) Nugent, W. A. J. Am. Chem. Soc. 1992, 114, 2768. (b) Bedeschi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897. (c) Yu, C.-M.; Yoon, S.-K.; Choi, H.-S.; Back, K. Chem. Commun. 1997, 763. (d) Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262.
32. Cox, P. J.; Wong, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253.
33. The aldol adduct was obtained as a free alcohol form mainly, while products were obtained as silylated forms in previous reports on catalytic asymmetric aldol reactions of silyl enolates.
34. Katsuki et al. reported a fluorinated alcohol accelerated catalytic asymmetric Michael reactions: (a) Kitajima, H.; Katsuki, T. Synlett 1997, 558. See also: (b) Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595. It should be noted in our case that an alcohol not only accelerates the catalyst regeneration step but also blocks an undesired achiral side reaction. See ref 4.
35. Katsuki et al. reported a fluorinated alcohol accelerated catalytic asymmetric Michael reactions: (a) Kitajima, H.; Katsuki, T. Synlett 1997, 558. See also: (b) Evans, D. A.; Johnson, D. S. Org. Lett. 1999, 1, 595. It should be noted in our case that an alcohol not only accelerates the catalyst regeneration step but also blocks an undesired achiral side reaction. See ref 4.
36. 2b
37. syn-Selective catalytic asymmetric aldol reactions were reported. Furuta, K.; Maruyama, T. Yamamoto, H. Synlett 1991, 439.
38. Bulky aliphatic aldehydes such as pivalaldehyde and isobutyraldehyde reacted with 2c sluggishly. While α-benzyloxyaldehyde reacted with 2c to afford the corresponding aldol adduct in a good yield (∼75%), lower selectivities were obtained (synlanti = ∼1/4, anti = ∼50% ee). Investigations to improve these lower yields and selectivities are in progress.
39. 6e In these reactions, both (E)- and (Z)-silyl enolates gave anti-adducts.
40. (a) Mukaiyama, T.; Kobayashi, S.; Murakami, M. Chem. Lett. 1985, 447.
41. (b) Gennari, C.; Beretta, M. G.; Bernardi, A.; Moro, G.; Scolastico, C.; Todeschini, R.; Tetrahedron 1986, 42, 893.
42. 2) δ 92.8, 95.0, 116.8, 119.0, 122.5, 123.1, 125.5, 125.6, 125.7, 126.0, 126.3, 126.8, 130.3, 130.4, 134.1, 134.2, 138.1, 139.4, 154.4, 156.1.
43. Details are shown in Supporting Information.