Chiral Lewis acid catalysis in aqueous media. Catalytic asymmetric aldol reactions of silyl enol ethers with aldehydes in a protic solvent including water

Chemistry Letters

Volumn , Issue 1, 1999, Pages 71-72

  Kobayashi, Shu ^a   Nagayama, Satoshi ^b   Busujima, Tsuyoshi ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033238967     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.71     Document Type: Article

References (41)

1. Review: H. Gröger, E. M. Vogl, and M. Shibasaki, Chem. Eur. J., 4, 1137 (1998); S. G. Nelson, Tetrahedron: Asym., 9, 357 (1998); T. Bach, Angew, Chem., Int. Ed. Engl., 33, 417 (1994).
2. Review: H. Gröger, E. M. Vogl, and M. Shibasaki, Chem. Eur. J., 4, 1137 (1998); S. G. Nelson, Tetrahedron: Asym., 9, 357 (1998); T. Bach, Angew, Chem., Int. Ed. Engl., 33, 417 (1994).
3. Review: H. Gröger, E. M. Vogl, and M. Shibasaki, Chem. Eur. J., 4, 1137 (1998); S. G. Nelson, Tetrahedron: Asym., 9, 357 (1998); T. Bach, Angew, Chem., Int. Ed. Engl., 33, 417 (1994).
4. T. Mukaiyama, K. Narasaka, and K. Banno, Chem. Lett., 1973, 1012.
5. S. Kobayashi, Y. Fujishita, and T. Mukaiyama, Chem. Lett., 1990, 1455; T. Mukaiyama, S. Kobayashi, H. Uchiro, and I. Shiina, Chem. Lett., 1990, 129.
6. S. Kobayashi, Y. Fujishita, and T. Mukaiyama, Chem. Lett., 1990, 1455; T. Mukaiyama, S. Kobayashi, H. Uchiro, and I. Shiina, Chem. Lett., 1990, 129.
7. Catalytic asymmetric aldol reactions in wet dimethylformamide were reported. M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995). Cf. K. Mikami, O. Kotera, Y. Motoyama, and H. Sakaguchi, Synlett, 1995, 975.
8. Catalytic asymmetric aldol reactions in wet dimethylformamide were reported. M. Sodeoka, K. Ohrai, and M. Shibasaki, J. Org. Chem., 60, 2648 (1995). Cf. K. Mikami, O. Kotera, Y. Motoyama, and H. Sakaguchi, Synlett, 1995, 975.
9. Some catalytic asymmetric aldol reactions were performed at higher temperatures (-20 - 23 °C). K. Mikami and S. Matsukawa, J. Am. Chem. Soc., 115, 7039 (1993); K. Mikami and S. Matsukawa, J. Am. Chem. Soc., 116, 4077 (1994); E. M. Carreira, R. A. Singer, and W. Lee, J. Am. Chem. Soc., 116, 8837 (1994); G. E. Keck and D. Krishnamurthy, J. Am. Chem. Soc., 117, 2363 (1995). See also Ref. 4.
10. Some catalytic asymmetric aldol reactions were performed at higher temperatures (-20 - 23 °C). K. Mikami and S. Matsukawa, J. Am. Chem. Soc., 115, 7039 (1993); K. Mikami and S. Matsukawa, J. Am. Chem. Soc., 116, 4077 (1994); E. M. Carreira, R. A. Singer, and W. Lee, J. Am. Chem. Soc., 116, 8837 (1994); G. E. Keck and D. Krishnamurthy, J. Am. Chem. Soc., 117, 2363 (1995). See also Ref. 4.
11. Some catalytic asymmetric aldol reactions were performed at higher temperatures (-20 - 23 °C). K. Mikami and S. Matsukawa, J. Am. Chem. Soc., 115, 7039 (1993); K. Mikami and S. Matsukawa, J. Am. Chem. Soc., 116, 4077 (1994); E. M. Carreira, R. A. Singer, and W. Lee, J. Am. Chem. Soc., 116, 8837 (1994); G. E. Keck and D. Krishnamurthy, J. Am. Chem. Soc., 117, 2363 (1995). See also Ref. 4.
12. Some catalytic asymmetric aldol reactions were performed at higher temperatures (-20 - 23 °C). K. Mikami and S. Matsukawa, J. Am. Chem. Soc., 115, 7039 (1993); K. Mikami and S. Matsukawa, J. Am. Chem. Soc., 116, 4077 (1994); E. M. Carreira, R. A. Singer, and W. Lee, J. Am. Chem. Soc., 116, 8837 (1994); G. E. Keck and D. Krishnamurthy, J. Am. Chem. Soc., 117, 2363 (1995). See also Ref. 4.
13. S. Kobayashi, Chem. Lett., 1991, 2187; S. Kobayashi and I. Hachiya, J. Org. Chem., 59, 3590 (1994); S. Kobayashi, Synlett, 1994, 689.
14. S. Kobayashi, Chem. Lett., 1991, 2187; S. Kobayashi and I. Hachiya, J. Org. Chem., 59, 3590 (1994); S. Kobayashi, Synlett, 1994, 689.
15. S. Kobayashi, Chem. Lett., 1991, 2187; S. Kobayashi and I. Hachiya, J. Org. Chem., 59, 3590 (1994); S. Kobayashi, Synlett, 1994, 689.
16. S. Kobayashi, in "Organic Reactions in Water," ed by P. Grieco, Chapman & Hall (1998), p. 262; S. Kobayashi, Pure Appl. Chem., 70, 1019 (1998).
17. S. Kobayashi, in "Organic Reactions in Water," ed by P. Grieco, Chapman & Hall (1998), p. 262; S. Kobayashi, Pure Appl. Chem., 70, 1019 (1998).
18. S. Kobayashi, S. Nagayama, and T. Busujima, 7. Am. Chem. Soc., 120, 8287 (1998).
19. Copper(II) was revealed to be one of the most promising metals. S. Kobayashi, S. Nagayama, and T. Busujima, Chem. Lett., 1997, 959. See also, Ref. 8.
20. H. Fritschi, U. Leutenegger, and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 25, 1005 (1986); H. Brunner and U. Obermann, Chem. Ber., 122, 499 (1989); H. Nishiyama, H. Sakaguchi, T. Nakamura, M. Horihata, M. Kondo, and K. Ito, Organometallics, 8, 821 (1989); G. Balavoine, J. C. Clinet, and I. Lellouche, Tetrahedron Lett., 30, 5141 (1989); R. E. Lowenthal, A. Abiko, and S. Masamune, Tetrahedron Lett., 31, 6005 (1990); D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991); E. J. Corey, N. Imai, and H.-Y. Zhang, 7. Am. Chem. Soc., 113, 728 (1991); D. Müller, G. Umbricht, B. Weber, and A. Pfaltz, Helv. Chim. Acta, 74, 232 (1991).
21. H. Fritschi, U. Leutenegger, and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 25, 1005 (1986); H. Brunner and U. Obermann, Chem. Ber., 122, 499 (1989); H. Nishiyama, H. Sakaguchi, T. Nakamura, M. Horihata, M. Kondo, and K. Ito, Organometallics, 8, 821 (1989); G. Balavoine, J. C. Clinet, and I. Lellouche, Tetrahedron Lett., 30, 5141 (1989); R. E. Lowenthal, A. Abiko, and S. Masamune, Tetrahedron Lett., 31, 6005 (1990); D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991); E. J. Corey, N. Imai, and H.-Y. Zhang, 7. Am. Chem. Soc., 113, 728 (1991); D. Müller, G. Umbricht, B. Weber, and A. Pfaltz, Helv. Chim. Acta, 74, 232 (1991).
22. H. Fritschi, U. Leutenegger, and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 25, 1005 (1986); H. Brunner and U. Obermann, Chem. Ber., 122, 499 (1989); H. Nishiyama, H. Sakaguchi, T. Nakamura, M. Horihata, M. Kondo, and K. Ito, Organometallics, 8, 821 (1989); G. Balavoine, J. C. Clinet, and I. Lellouche, Tetrahedron Lett., 30, 5141 (1989); R. E. Lowenthal, A. Abiko, and S. Masamune, Tetrahedron Lett., 31, 6005 (1990); D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991); E. J. Corey, N. Imai, and H.-Y. Zhang, 7. Am. Chem. Soc., 113, 728 (1991); D. Müller, G. Umbricht, B. Weber, and A. Pfaltz, Helv. Chim. Acta, 74, 232 (1991).
23. H. Fritschi, U. Leutenegger, and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 25, 1005 (1986); H. Brunner and U. Obermann, Chem. Ber., 122, 499 (1989); H. Nishiyama, H. Sakaguchi, T. Nakamura, M. Horihata, M. Kondo, and K. Ito, Organometallics, 8, 821 (1989); G. Balavoine, J. C. Clinet, and I. Lellouche, Tetrahedron Lett., 30, 5141 (1989); R. E. Lowenthal, A. Abiko, and S. Masamune, Tetrahedron Lett., 31, 6005 (1990); D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991); E. J. Corey, N. Imai, and H.-Y. Zhang, 7. Am. Chem. Soc., 113, 728 (1991); D. Müller, G. Umbricht, B. Weber, and A. Pfaltz, Helv. Chim. Acta, 74, 232 (1991).
24. H. Fritschi, U. Leutenegger, and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 25, 1005 (1986); H. Brunner and U. Obermann, Chem. Ber., 122, 499 (1989); H. Nishiyama, H. Sakaguchi, T. Nakamura, M. Horihata, M. Kondo, and K. Ito, Organometallics, 8, 821 (1989); G. Balavoine, J. C. Clinet, and I. Lellouche, Tetrahedron Lett., 30, 5141 (1989); R. E. Lowenthal, A. Abiko, and S. Masamune, Tetrahedron Lett., 31, 6005 (1990); D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991); E. J. Corey, N. Imai, and H.-Y. Zhang, 7. Am. Chem. Soc., 113, 728 (1991); D. Müller, G. Umbricht, B. Weber, and A. Pfaltz, Helv. Chim. Acta, 74, 232 (1991).
25. H. Fritschi, U. Leutenegger, and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 25, 1005 (1986); H. Brunner and U. Obermann, Chem. Ber., 122, 499 (1989); H. Nishiyama, H. Sakaguchi, T. Nakamura, M. Horihata, M. Kondo, and K. Ito, Organometallics, 8, 821 (1989); G. Balavoine, J. C. Clinet, and I. Lellouche, Tetrahedron Lett., 30, 5141 (1989); R. E. Lowenthal, A. Abiko, and S. Masamune, Tetrahedron Lett., 31, 6005 (1990); D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991); E. J. Corey, N. Imai, and H.-Y. Zhang, 7. Am. Chem. Soc., 113, 728 (1991); D. Müller, G. Umbricht, B. Weber, and A. Pfaltz, Helv. Chim. Acta, 74, 232 (1991).
26. H. Fritschi, U. Leutenegger, and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 25, 1005 (1986); H. Brunner and U. Obermann, Chem. Ber., 122, 499 (1989); H. Nishiyama, H. Sakaguchi, T. Nakamura, M. Horihata, M. Kondo, and K. Ito, Organometallics, 8, 821 (1989); G. Balavoine, J. C. Clinet, and I. Lellouche, Tetrahedron Lett., 30, 5141 (1989); R. E. Lowenthal, A. Abiko, and S. Masamune, Tetrahedron Lett., 31, 6005 (1990); D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991); E. J. Corey, N. Imai, and H.-Y. Zhang, 7. Am. Chem. Soc., 113, 728 (1991); D. Müller, G. Umbricht, B. Weber, and A. Pfaltz, Helv. Chim. Acta, 74, 232 (1991).
27. H. Fritschi, U. Leutenegger, and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 25, 1005 (1986); H. Brunner and U. Obermann, Chem. Ber., 122, 499 (1989); H. Nishiyama, H. Sakaguchi, T. Nakamura, M. Horihata, M. Kondo, and K. Ito, Organometallics, 8, 821 (1989); G. Balavoine, J. C. Clinet, and I. Lellouche, Tetrahedron Lett., 30, 5141 (1989); R. E. Lowenthal, A. Abiko, and S. Masamune, Tetrahedron Lett., 31, 6005 (1990); D. A. Evans, K. A. Woerpel, M. M. Hinman, and M. M. Faul, J. Am. Chem. Soc., 113, 726 (1991); E. J. Corey, N. Imai, and H.-Y. Zhang, 7. Am. Chem. Soc., 113, 728 (1991); D. Müller, G. Umbricht, B. Weber, and A. Pfaltz, Helv. Chim. Acta, 74, 232 (1991).
28. Similar copper(II) complexes were used in some catalytic asymmetric reactions in organic solvents. D. A. Evans, G. S. Peterson, J. S. Johnson, D. M. Barnes, K. R. Campos, and K. A. Woerpel, J. Org. Chem., 63, 4541 (1998), and references cited therein.
29. Catalytic asymmetric aldol reactions of silyl enolates with (benzyloxy)acetaldehyde or α-ketoeslers using similar copper(II) complexes in anhydrous organic solvents were reported. Low selectivities in the reaction of benzaldehyde or dihydrocinnamaldehyde with the silyl enolate derived from t-butyl thioacetate were indicated. D. A. Evans, J. A. Murry, and M. C. Kozlowski, J. Am. Chem. Soc., 118, 5814 (1996); D. A. Evans, M. C. Kozlowski, C. S. Burgey, and D. W. C. MacMillan, J. Am. Chem. Soc., 119, 7893 (1997).
30. Catalytic asymmetric aldol reactions of silyl enolates with (benzyloxy)acetaldehyde or α-ketoeslers using similar copper(II) complexes in anhydrous organic solvents were reported. Low selectivities in the reaction of benzaldehyde or dihydrocinnamaldehyde with the silyl enolate derived from t-butyl thioacetate were indicated. D. A. Evans, J. A. Murry, and M. C. Kozlowski, J. Am. Chem. Soc., 118, 5814 (1996); D. A. Evans, M. C. Kozlowski, C. S. Burgey, and D. W. C. MacMillan, J. Am. Chem. Soc., 119, 7893 (1997).
31. Although yields and selectivities are moderate in some cases, these are not optimized and will be improved by designing chiral ligands.
32. Reverse enantioselectivity was observed.
33. Only a trace amount of the adduct was detected when the reaction was carried out in dichloromethane at -78 °C.
34. E. M. Carreira and R. A. Singer, Tetrahedron Lett., 25, 4323 (1994); S. E. Denmark and C.-T. Chen, Tetrahedron Lett., 25, 4327 (1994); T. K. Hollis and B. Bosnich, J. Am. Chem. Soc., 117, 4570 (1995); M. Oishi, S. Aratake, and H. Yamamoto, J. Am. Chem. Soc., 120, 8271 (1998) See also, S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 119, 10049 (1997).
35. E. M. Carreira and R. A. Singer, Tetrahedron Lett., 25, 4323 (1994); S. E. Denmark and C.-T. Chen, Tetrahedron Lett., 25, 4327 (1994); T. K. Hollis and B. Bosnich, J. Am. Chem. Soc., 117, 4570 (1995); M. Oishi, S. Aratake, and H. Yamamoto, J. Am. Chem. Soc., 120, 8271 (1998) See also, S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 119, 10049 (1997).
36. E. M. Carreira and R. A. Singer, Tetrahedron Lett., 25, 4323 (1994); S. E. Denmark and C.-T. Chen, Tetrahedron Lett., 25, 4327 (1994); T. K. Hollis and B. Bosnich, J. Am. Chem. Soc., 117, 4570 (1995); M. Oishi, S. Aratake, and H. Yamamoto, J. Am. Chem. Soc., 120, 8271 (1998) See also, S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 119, 10049 (1997).
37. E. M. Carreira and R. A. Singer, Tetrahedron Lett., 25, 4323 (1994); S. E. Denmark and C.-T. Chen, Tetrahedron Lett., 25, 4327 (1994); T. K. Hollis and B. Bosnich, J. Am. Chem. Soc., 117, 4570 (1995); M. Oishi, S. Aratake, and H. Yamamoto, J. Am. Chem. Soc., 120, 8271 (1998) See also, S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 119, 10049 (1997).
38. E. M. Carreira and R. A. Singer, Tetrahedron Lett., 25, 4323 (1994); S. E. Denmark and C.-T. Chen, Tetrahedron Lett., 25, 4327 (1994); T. K. Hollis and B. Bosnich, J. Am. Chem. Soc., 117, 4570 (1995); M. Oishi, S. Aratake, and H. Yamamoto, J. Am. Chem. Soc., 120, 8271 (1998) . See also, S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 119, 10049 (1997).
39. Similar results were obtained using 20% water/ethanol solutions.
40. Quite recently, Engberts et al. reported an asymmetric Diels-Alder reaction using a chiral Lewis acid in water. S. Otto, G. Boccaletti, and J. B. F. N. Engberts, 7. Am. Chem. Soc., 120, 4238 (1998).
41. S. E. Denmark, K.-T. Wong, and R. A. Stavenger, J. Am. Chem. Soc., 119, 2333 (1997).