Asymmetric catalysis with chiral Lewis bases

Pure and Applied Chemistry

Volumn 70, Issue 8, 1998, Pages 1469-1476

  Denmark, Scott E ^a   Stavenger, Robert A ^a   Su, Xiping ^a   Wong, Ken Tsung ^a   Nishigaichi, Yutaka ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001593533     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199870081469     Document Type: Article

References (32)

1. For reviews on catalytic asymmetric aldol additions, see (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317-416. (c) Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653-668. (d) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993; pp 367-388. (e) Yamamoto, H.; Maruoka, K.; Ishihara, K. J. Synth. Org. Jpn. 1994, 52, 912. (f) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); Edition E21; Helmchen, G.; Hoffman, R., Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1996; Vol. 3; pp 1730-1736.
2. For reviews on catalytic asymmetric aldol additions, see (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317-416. (c) Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653-668. (d) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993; pp 367-388. (e) Yamamoto, H.; Maruoka, K.; Ishihara, K. J. Synth. Org. Jpn. 1994, 52, 912. (f) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); Edition E21; Helmchen, G.; Hoffman, R., Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1996; Vol. 3; pp 1730-1736.
3. For reviews on catalytic asymmetric aldol additions, see (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317-416. (c) Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653-668. (d) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993; pp 367-388. (e) Yamamoto, H.; Maruoka, K.; Ishihara, K. J. Synth. Org. Jpn. 1994, 52, 912. (f) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); Edition E21; Helmchen, G.; Hoffman, R., Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1996; Vol. 3; pp 1730-1736.
4. For reviews on catalytic asymmetric aldol additions, see (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317-416. (c) Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653-668. (d) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993; pp 367-388. (e) Yamamoto, H.; Maruoka, K.; Ishihara, K. J. Synth. Org. Jpn. 1994, 52, 912. (f) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); Edition E21; Helmchen, G.; Hoffman, R., Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1996; Vol. 3; pp 1730-1736.
5. For reviews on catalytic asymmetric aldol additions, see (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317-416. (c) Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653-668. (d) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993; pp 367-388. (e) Yamamoto, H.; Maruoka, K.; Ishihara, K. J. Synth. Org. Jpn. 1994, 52, 912. (f) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); Edition E21; Helmchen, G.; Hoffman, R., Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1996; Vol. 3; pp 1730-1736.
6. For reviews on catalytic asymmetric aldol additions, see (a) Bach, T. Angew. Chem., Int. Ed. Engl. 1994, 33, 417. (b) Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317-416. (c) Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653-668. (d) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993; pp 367-388. (e) Yamamoto, H.; Maruoka, K.; Ishihara, K. J. Synth. Org. Jpn. 1994, 52, 912. (f) Braun, M. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); Edition E21; Helmchen, G.; Hoffman, R., Mulzer, J.; Schaumann, E. Eds.; Thieme: Stuttgart, 1996; Vol. 3; pp 1730-1736.
7. For leading references on catalytic asymmetric aldol additions see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (c) Nelson, S. G. Tetrahedron : Asymmetry 1998, 9, 357.
8. For leading references on catalytic asymmetric aldol additions see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (c) Nelson, S. G. Tetrahedron : Asymmetry 1998, 9, 357.
9. For leading references on catalytic asymmetric aldol additions see: (a) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (b) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871. (c) Nelson, S. G. Tetrahedron : Asymmetry 1998, 9, 357.
10. For examples of primarily anti-selective catalytic asymmetric aldol additions, see: (a) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. (b) Kobayashi, S.; Horibe, M.; Hachiya, I. Tetrahedron Lett. 1995, 36, 3173.
11. For examples of primarily anti-selective catalytic asymmetric aldol additions, see: (a) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859. (b) Kobayashi, S.; Horibe, M.; Hachiya, I. Tetrahedron Lett. 1995, 36, 3173.
12. (a) Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404.
13. (b) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333.
14. (c) Denmark, S. E.; Winter, S. B. D. Synlett 1997, 1087.
15. (d) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918.
16. (e) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. Tetrahedron 1998, 0000.
17. (a) Burlachenko, G. S.; Khasapov, B. N.; Petrovskaya, L. I.; Baukov, Yu. I.; Lutsenko, I. F. J. Gen. Chem. USSR (Engl. Transl.) 1966, 36, 532.
18. (b) Lutsenko, I. F.; Baukov, Yu. I.; Burlachenko, G. S.; Khasapov, B. N. J. Organomet. Chem. 1966, 5, 20.
19. (c) Burlachenko, G. S.; Baukov, Yu. I.; Dzherayan, T. G.; Lutsenko, I. F. J. Gen. Chem. USSR (Engl. Transl.) 1975, 45, 73.
20. (d) Baukov, Yu. I.; Lutsenko, I. F. Moscow Univ. Chem. Bull. (Engl. Transl.) 1970, 25, 72.
21. (e) Ponomarev, S. V.; Baukov, Yu. I.; Dudukma O. V.; Petrosyan, I. V.; Petrovskaya, L. I. J. Gen. Chem. USSR (Engl. Transl.) 1967, 37, 2092.
22. (f) Benkeser, R. A.; Smith, W. E. J. Am. Chem. Soc. 1968, 90, 5307.
23. (g) Burlachenko, G. S.; Baukov, Yu. I.; Lutsenko, I. F. J. Gen. Chem. USSR (Engl. Transl.) 1970, 40, 88.
24. 2 as an electrofugal group. For examples of the synthesis of α-mercurio ketones from silyl enol ethers see: (a) House, H. O.; Auerbach, R. A.; Gall, M.; Peet, N. P. J. Org. Chem. 1973, 38, 514. (b) Yamamoto, Y.; Maruyama, K. J. Am. Chem. Soc. 1982, 104, 2323. (c) Bluthe, N.; Malacria, M.; Gore, J. Tetrahedron 1984, 40, 3277. (d) Drouin, J.; Boaventura, M.-A.; Conia, J.-M. J. Am. Chem. Soc. 1985, 107, 1726.
25. 2 as an electrofugal group. For examples of the synthesis of α-mercurio ketones from silyl enol ethers see: (a) House, H. O.; Auerbach, R. A.; Gall, M.; Peet, N. P. J. Org. Chem. 1973, 38, 514. (b) Yamamoto, Y.; Maruyama, K. J. Am. Chem. Soc. 1982, 104, 2323. (c) Bluthe, N.; Malacria, M.; Gore, J. Tetrahedron 1984, 40, 3277. (d) Drouin, J.; Boaventura, M.-A.; Conia, J.-M. J. Am. Chem. Soc. 1985, 107, 1726.
26. 2 as an electrofugal group. For examples of the synthesis of α-mercurio ketones from silyl enol ethers see: (a) House, H. O.; Auerbach, R. A.; Gall, M.; Peet, N. P. J. Org. Chem. 1973, 38, 514. (b) Yamamoto, Y.; Maruyama, K. J. Am. Chem. Soc. 1982, 104, 2323. (c) Bluthe, N.; Malacria, M.; Gore, J. Tetrahedron 1984, 40, 3277. (d) Drouin, J.; Boaventura, M.-A.; Conia, J.-M. J. Am. Chem. Soc. 1985, 107, 1726.
27. 2 as an electrofugal group. For examples of the synthesis of α-mercurio ketones from silyl enol ethers see: (a) House, H. O.; Auerbach, R. A.; Gall, M.; Peet, N. P. J. Org. Chem. 1973, 38, 514. (b) Yamamoto, Y.; Maruyama, K. J. Am. Chem. Soc. 1982, 104, 2323. (c) Bluthe, N.; Malacria, M.; Gore, J. Tetrahedron 1984, 40, 3277. (d) Drouin, J.; Boaventura, M.-A.; Conia, J.-M. J. Am. Chem. Soc. 1985, 107, 1726.
28. Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161.
29. We have previously demonstrated that the E-enolate to syn adduct correlation is characteristic of uncatalyzed aldol reactions of enoxysilacyclobutanes. The putative pentacoordinate siliconate transition structures were shown computationally to prefer boat-like arrangements in this array. Denmark, S. E.; Griedel, B. D.; Coe, D. M.; Schnute M. E. J. Am. Chem. Soc. 1994, 116, 7026.
30. For reviews of the aldol reaction of boron enolates see: (a) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehesive Organic Synthesis: Additions to C-X π-Bonds Part 2; Heathcock, C. H., Ed. Pergamon Press: Oxford, 1991; Chapt. 1.7. (b) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
31. For reviews of the aldol reaction of boron enolates see: (a) Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehesive Organic Synthesis: Additions to C-X π-Bonds Part 2; Heathcock, C. H., Ed. Pergamon Press: Oxford, 1991; Chapt. 1.7. (b) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
32. Bent, H. A. Chem. Rev. 1961, 61, 275.