Enantioselective Michael additions to α,β-unsaturated imides catalyzed by a salen-al complex

Journal of the American Chemical Society

Volumn 125, Issue 37, 2003, Pages 11204-11205

  Taylor, Mark S ^a   Jacobsen, Eric N ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALKYL GROUP; ALUMINUM; BUTYRIC ACID DERIVATIVE; CARBON; CARBONYL DERIVATIVE; CYCLOHEXANE; IMIDE; MALONONITRILE; PAROXETINE; SOLVENT;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

ALUMINUM; CATALYSIS; CHELATING AGENTS; ETHYLENEDIAMINES; IMIDES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PAROXETINE; SEROTONIN UPTAKE INHIBITORS;

EID: 0141725892     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037177o     Document Type: Article

References (32)

1. For reviews, see: (a) Tomioka, K.; Nagaoka, Y.; Yamaguchi, M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, Chapters 31.1 and 31.2.
2. (b) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196.
3. Enantioselective conjugate addition of malonates to (a) acyclic enals and enones: Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1173-1175. Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (b) chalcone: End, N.; Macko, L.; Zehnder, M.; Pfaltz, A. Chem.-Eur. J. 1998, 4, 818-824. (c) Addition of β-dicarbonyl compounds to cyclic enones: Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572. Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104-106.
4. Enantioselective conjugate addition of malonates to (a) acyclic enals and enones: Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1173-1175. Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (b) chalcone: End, N.; Macko, L.; Zehnder, M.; Pfaltz, A. Chem.-Eur. J. 1998, 4, 818-824. (c) Addition of β-dicarbonyl compounds to cyclic enones: Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572. Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104-106.
5. Enantioselective conjugate addition of malonates to (a) acyclic enals and enones: Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1173-1175. Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (b) chalcone: End, N.; Macko, L.; Zehnder, M.; Pfaltz, A. Chem.-Eur. J. 1998, 4, 818-824. (c) Addition of β-dicarbonyl compounds to cyclic enones: Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572. Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104-106.
6. Enantioselective conjugate addition of malonates to (a) acyclic enals and enones: Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1173-1175. Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (b) chalcone: End, N.; Macko, L.; Zehnder, M.; Pfaltz, A. Chem.-Eur. J. 1998, 4, 818-824. (c) Addition of β-dicarbonyl compounds to cyclic enones: Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572. Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104-106.
7. Enantioselective conjugate addition of malonates to (a) acyclic enals and enones: Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1173-1175. Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (b) chalcone: End, N.; Macko, L.; Zehnder, M.; Pfaltz, A. Chem.-Eur. J. 1998, 4, 818-824. (c) Addition of β-dicarbonyl compounds to cyclic enones: Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572. Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104-106.
8. Enantioselective conjugate addition of malonates to (a) acyclic enals and enones: Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1173-1175. Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2003, 42, 661-665. (b) chalcone: End, N.; Macko, L.; Zehnder, M.; Pfaltz, A. Chem.-Eur. J. 1998, 4, 818-824. (c) Addition of β-dicarbonyl compounds to cyclic enones: Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571-1572. Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. Arai, T.; Sasai, H.; Aoe, K.; Okamura, K.; Date, T.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 104-106.
9. Enantioselective conjugate additions of nitroalkanes to (a) N-acylpyrazoles: Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394-13395. (b) acyclic enones: Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331-8338. (c) chalcones: Funabashi, K.; Saida, Y.; Kanai, M.; Arai, T.; Sasi, H.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7557-7558.
10. Enantioselective conjugate additions of nitroalkanes to (a) N-acylpyrazoles: Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394-13395. (b) acyclic enones: Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331-8338. (c) chalcones: Funabashi, K.; Saida, Y.; Kanai, M.; Arai, T.; Sasi, H.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7557-7558.
11. Enantioselective conjugate additions of nitroalkanes to (a) N-acylpyrazoles: Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394-13395. (b) acyclic enones: Halland, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2002, 67, 8331-8338. (c) chalcones: Funabashi, K.; Saida, Y.; Kanai, M.; Arai, T.; Sasi, H.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7557-7558.
12. 3: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959-8960. (b) HCN: Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442-4443. (c) thiols: Chen, Q.; Jacobsen, E. N., manuscript in preparation. (d) salen-Red-Al-catalyzed Michael additions to ketones have been described: Jha, S. C.; Joshi, N. N. Tetrahedron: Asymmetry 2001, 12, 2463-2466.
13. 3: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959-8960. (b) HCN: Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442-4443. (c) thiols: Chen, Q.; Jacobsen, E. N., manuscript in preparation. (d) salen-Red-Al-catalyzed Michael additions to ketones have been described: Jha, S. C.; Joshi, N. N. Tetrahedron: Asymmetry 2001, 12, 2463-2466.
14. 3: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959-8960. (b) HCN: Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442-4443. (c) thiols: Chen, Q.; Jacobsen, E. N., manuscript in preparation. (d) salen-Red-Al-catalyzed Michael additions to ketones have been described: Jha, S. C.; Joshi, N. N. Tetrahedron: Asymmetry 2001, 12, 2463-2466.
15. 3: Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959-8960. (b) HCN: Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442-4443. (c) thiols: Chen, Q.; Jacobsen, E. N., manuscript in preparation. (d) salen-Red-Al-catalyzed Michael additions to ketones have been described: Jha, S. C.; Joshi, N. N. Tetrahedron: Asymmetry 2001, 12, 2463-2466.
16. The screen included β-ketoesters, malonates, nitroalkanes, and sulfones; nitrile-substituted substrates proved uniquely effective in reactions catalyzed by 1.
17. Catalyst 1 is a bench-stable complex prepared by partial hydrolysis of the corresponding (salen)AlMe derivative. (a) Rutherford, D.; Atwood, D. A. Organometallics 1996, 15, 4417-4422. For related complexes, see: (b) Dzugan, S. J.; Goedken, V. L. Inorg. Chem. 1986, 25, 2858. (c) Gurian, P. L.; Cheatham, L. K.; Ziller, J. W.; Barron, A. R. J. Chem. Soc., Dalton Trans. 1991, 1449-1456.
18. Catalyst 1 is a bench-stable complex prepared by partial hydrolysis of the corresponding (salen)AlMe derivative. (a) Rutherford, D.; Atwood, D. A. Organometallics 1996, 15, 4417-4422. For related complexes, see: (b) Dzugan, S. J.; Goedken, V. L. Inorg. Chem. 1986, 25, 2858. (c) Gurian, P. L.; Cheatham, L. K.; Ziller, J. W.; Barron, A. R. J. Chem. Soc., Dalton Trans. 1991, 1449-1456.
19. Catalyst 1 is a bench-stable complex prepared by partial hydrolysis of the corresponding (salen)AlMe derivative. (a) Rutherford, D.; Atwood, D. A. Organometallics 1996, 15, 4417-4422. For related complexes, see: (b) Dzugan, S. J.; Goedken, V. L. Inorg. Chem. 1986, 25, 2858. (c) Gurian, P. L.; Cheatham, L. K.; Ziller, J. W.; Barron, A. R. J. Chem. Soc., Dalton Trans. 1991, 1449-1456.
20. The origin of the rate acceleration imparted by tert-butyl alcohol has not been ascertained. However, promotion of turnover of aluminum enolate intermediates represents a likely role. For a general discussion of the use of achiral additives in asymmetric catalysis: Vogl, E. M.; Gröger, H.; Shibasaki, M. Angew. Chem., Int. Ed. 1999, 38, 1570-1577.
21. For other examples, see: (a) Hermann, K.; Wynberg, H. J. Org. Chem. 1979, 44, 2238-2244.
22. (b) Sasai, H.; Emori, E.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 5561-5564.
23. (c) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240-11241.
24. (d) Sawamura, M.; Hamashima, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295-8296.
25. (e) Sawamura, M.; Hamashima, H.; Shinoto, H.; Ito, Y. Tetrahedron Lett. 1995, 36, 6479-6482.
26. (f) Review: Christoffers, J.; Baro, A. Angew. Chem., Int. Ed. 2003, 42, 1688-1690.
27. Krapcho, A. P. Synthesis 1982, 805-822, 893-913.
28. 3-catalyzed regioselective methanolysis of imides, see: Evans, D. A.; Trotter, B. W.; Coleman, P. J.; Côté, B.; Dias, L. C.; Rajapakse, H. A.; Tyler, A. N. Tetrahedron 1999, 55, 8671-8726.
29. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
30. The Sumigo route incorporates a racemic conjugate addition and a late stage resolution. Sugi, K.; Itaya, N.; Katsura, T.; Igi, M.; Yamazaki, S.; Ishibashi, T.; Yamaoka, T.; Kawada, Y.; Tagami, Y.; Otsuki, M.; Oshima, T. Chem. Pharm. Bull. 2000, 48, 529-536.
31. All characterization data, including optical rotation, were in agreement with literature values (ref 12).
32. For a prior asymmetric catalytic synthesis of paroxotine employing an enzymatic desymmetrization as the key step, see: Yu, M.; Lantos, I.; Peng, Z.; Yu, J.; Cacchio, T. Tetrahedron Lett. 2000, 41, 5647-5651. For other syntheses of paroxetine, see references therein.