Lewis Base-Catalyzed, Asymmetric Aldol Additions of Methyl Ketone Enolates

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 918-919

  Denmark, Scott E ^a   Stavenger, Robert A ^a   Wong, Ken Tsung ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001126230     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972168h     Document Type: Article

References (31)

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. (c) Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653. (d) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993; p 367. (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., Hoffmann, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3; p 1730.
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. (c) Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653. (d) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993; p 367. (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., Hoffmann, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3; p 1730.
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. (c) Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653. (d) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993; p 367. (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., Hoffmann, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3; p 1730.
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. (c) Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653. (d) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993; p 367. (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., Hoffmann, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3; p 1730.
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. (c) Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653. (d) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993; p 367. (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., Hoffmann, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3; p 1730.
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. (c) Braun, M.; Sacha, H. J. Prakt. Chem. 1993, 335, 653. (d) Sawamura, M.; Ito, Y. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH: New York, 1993; p 367. (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., Hoffmann, R., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1996; Vol. 3; p 1730.
7. (a) Denmark, S. E.; Lee, W. J. Org. Chem. 1994, 59, 707.
8. (b) Kobayashi, S.; Horibe, M. Chem. Eur. J. 1997, 3, 1472.
9. For a specific example, see: Kiyooka, S.-i.; Hena, M. A. Tetrahedron: Asymmetry 1996, 7, 2181.
10. (a) Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404.
11. (b) Denmark, S. E.; Winter, S. B. D. Synlett 1997, 1087.
12. Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333.
13. For examples of other catalytic asymmetric aldol additions of methyl ketones, see: (a) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (b) Ishihara, K.; Maruyama, T.; Mouri, M.; Gao, Q.; Furuta, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 3483. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. (e) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (f) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (g) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (h) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
14. For examples of other catalytic asymmetric aldol additions of methyl ketones, see: (a) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (b) Ishihara, K.; Maruyama, T.; Mouri, M.; Gao, Q.; Furuta, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 3483. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. (e) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (f) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (g) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (h) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
15. For examples of other catalytic asymmetric aldol additions of methyl ketones, see: (a) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (b) Ishihara, K.; Maruyama, T.; Mouri, M.; Gao, Q.; Furuta, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 3483. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. (e) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (f) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (g) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (h) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
16. For examples of other catalytic asymmetric aldol additions of methyl ketones, see: (a) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (b) Ishihara, K.; Maruyama, T.; Mouri, M.; Gao, Q.; Furuta, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 3483. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. (e) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (f) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (g) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (h) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
17. For examples of other catalytic asymmetric aldol additions of methyl ketones, see: (a) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (b) Ishihara, K.; Maruyama, T.; Mouri, M.; Gao, Q.; Furuta, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 3483. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. (e) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (f) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (g) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (h) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
18. For examples of other catalytic asymmetric aldol additions of methyl ketones, see: (a) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (b) Ishihara, K.; Maruyama, T.; Mouri, M.; Gao, Q.; Furuta, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 3483. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. (e) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (f) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (g) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (h) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
19. For examples of other catalytic asymmetric aldol additions of methyl ketones, see: (a) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (b) Ishihara, K.; Maruyama, T.; Mouri, M.; Gao, Q.; Furuta, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 3483. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. (e) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (f) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (g) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (h) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
20. For examples of other catalytic asymmetric aldol additions of methyl ketones, see: (a) Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907. (b) Ishihara, K.; Maruyama, T.; Mouri, M.; Gao, Q.; Furuta, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 3483. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039. (d) Carreira, E. M.; Lee, W.; Singer, R. A. J. Am. Chem. Soc. 1995, 117, 3649. (e) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463. (f) Ando, A.; Miura, T.; Tatematsu, T.; Shioiri, T. Tetrahedron Lett. 1993, 34, 1507. (g) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319. (h) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
21. Benkeser, R. A.; Smith, W. E. J. Am. Chem. Soc. 1968, 90, 5307.
22. 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.
23. 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.
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. All new compounds were fully characterized by spectroscopic and analytical methods. See the Supporting Information.
27. Although the TMS enol ether derived from acetone is a good substrate for this reaction, removing TMSCl from the volatile enolate 3a proved difficult, and the modified Benkeser procedure was utilized for the synthesis of this enolate.
28. We assume that these reactions are proceeding though boatlike closed transition structures as previously demonstrated for Lewis acidic silyl (trichlorosilyl and silacyclobutyl) enolates. See: Denmark, S. E.; Griedel, B. D.; Coe, D. M.; Schnute, M. E. J. Am. Chem. Soc. 1994, 116, 7026.
29. Control experiments revealed that the reaction proceeds only marginally under the conditions of the standard catalyzed reaction (0.5 M, -78°C, 2 h) in the absence of catalyst. With aldehyde 8 and enolate 3b, only 4% of the aldol adduct 14 and 95% of unchanged 8 were isolated (cf. Table 5, entry 4).
30. Single-crystal X-ray analysis of the 4-bromobenzoate derived from (-)-14 established the absolute configuration of the major enantiomer to be S. All other configurational assignments were made by analogy.
31. 4 we believe that these reactions also proceed through closed, chairlike transition states organized around a hexacoordinate silicon atom.