Efficient Cu-catalyzed asymmetric conjugate additions of alkylzinc reagents to aromatic and aliphatic acyclic nitroalkenes

Organic Letters

Volumn 6, Issue 16, 2004, Pages 2829-2832

  Mampreian, Dawn M ^a   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC COMPOUND; ALKENE DERIVATIVE; AROMATIC COMPOUND; COPPER; NITRO DERIVATIVE; ZINC DERIVATIVE;

ADDITION LINE; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CONJUGATION; ENANTIOSELECTIVITY; ENVIRONMENTAL TEMPERATURE; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

ALKENES; ALKYLATION; AMINES; CATALYSIS; COPPER; CYCLOPARAFFINS; INDICATORS AND REAGENTS; LIGANDS; NITRO COMPOUNDS; ORGANOMETALLIC COMPOUNDS; ZINC;

EID: 4344701107     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0488338     Document Type: Article

References (27)

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5. For related reviews, see: (a) Krause, N.; Hoffmann-Roder, A. Synlett 2001, 171-196. (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 224-258. For representative recent reports, see: (d) Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (e) Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79-80. (f) Versleijen, J. P. G.; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (g) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778. (h) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700-3701. (i) Ongeri, S.; Piarulli, U.; Jackson, R. F. W.; Gennari, C. Eur. J. Org. Chem. 2001, 803-807. (j) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (k) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. Eilitz, U.; Lessmann, F.; Seidelmann, O.; Wendisch, V. Tetrahedron: Asymmetry 2003, 14, 189-191.
6. For related reviews, see: (a) Krause, N.; Hoffmann-Roder, A. Synlett 2001, 171-196. (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 224-258. For representative recent reports, see: (d) Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (e) Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79-80. (f) Versleijen, J. P. G.; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (g) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778. (h) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700-3701. (i) Ongeri, S.; Piarulli, U.; Jackson, R. F. W.; Gennari, C. Eur. J. Org. Chem. 2001, 803-807. (j) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (k) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. Eilitz, U.; Lessmann, F.; Seidelmann, O.; Wendisch, V. Tetrahedron: Asymmetry 2003, 14, 189-191.
7. For related reviews, see: (a) Krause, N.; Hoffmann-Roder, A. Synlett 2001, 171-196. (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 224-258. For representative recent reports, see: (d) Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (e) Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79-80. (f) Versleijen, J. P. G.; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (g) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778. (h) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700-3701. (i) Ongeri, S.; Piarulli, U.; Jackson, R. F. W.; Gennari, C. Eur. J. Org. Chem. 2001, 803-807. (j) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (k) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. Eilitz, U.; Lessmann, F.; Seidelmann, O.; Wendisch, V. Tetrahedron: Asymmetry 2003, 14, 189-191.
8. For related reviews, see: (a) Krause, N.; Hoffmann-Roder, A. Synlett 2001, 171-196. (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 224-258. For representative recent reports, see: (d) Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (e) Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79-80. (f) Versleijen, J. P. G.; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (g) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778. (h) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700-3701. (i) Ongeri, S.; Piarulli, U.; Jackson, R. F. W.; Gennari, C. Eur. J. Org. Chem. 2001, 803-807. (j) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (k) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. Eilitz, U.; Lessmann, F.; Seidelmann, O.; Wendisch, V. Tetrahedron: Asymmetry 2003, 14, 189-191.
9. For related reviews, see: (a) Krause, N.; Hoffmann-Roder, A. Synlett 2001, 171-196. (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 224-258. For representative recent reports, see: (d) Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (e) Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79-80. (f) Versleijen, J. P. G.; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (g) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778. (h) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700-3701. (i) Ongeri, S.; Piarulli, U.; Jackson, R. F. W.; Gennari, C. Eur. J. Org. Chem. 2001, 803-807. (j) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (k) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. Eilitz, U.; Lessmann, F.; Seidelmann, O.; Wendisch, V. Tetrahedron: Asymmetry 2003, 14, 189-191.
10. For related reviews, see: (a) Krause, N.; Hoffmann-Roder, A. Synlett 2001, 171-196. (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 224-258. For representative recent reports, see: (d) Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (e) Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79-80. (f) Versleijen, J. P. G.; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (g) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778. (h) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700-3701. (i) Ongeri, S.; Piarulli, U.; Jackson, R. F. W.; Gennari, C. Eur. J. Org. Chem. 2001, 803-807. (j) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (k) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. Eilitz, U.; Lessmann, F.; Seidelmann, O.; Wendisch, V. Tetrahedron: Asymmetry 2003, 14, 189-191.
11. For related reviews, see: (a) Krause, N.; Hoffmann-Roder, A. Synlett 2001, 171-196. (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 224-258. For representative recent reports, see: (d) Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (e) Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79-80. (f) Versleijen, J. P. G.; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (g) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778. (h) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700-3701. (i) Ongeri, S.; Piarulli, U.; Jackson, R. F. W.; Gennari, C. Eur. J. Org. Chem. 2001, 803-807. (j) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (k) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. Eilitz, U.; Lessmann, F.; Seidelmann, O.; Wendisch, V. Tetrahedron: Asymmetry 2003, 14, 189-191.
12. For related reviews, see: (a) Krause, N.; Hoffmann-Roder, A. Synlett 2001, 171-196. (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 224-258. For representative recent reports, see: (d) Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (e) Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79-80. (f) Versleijen, J. P. G.; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (g) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778. (h) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700-3701. (i) Ongeri, S.; Piarulli, U.; Jackson, R. F. W.; Gennari, C. Eur. J. Org. Chem. 2001, 803-807. (j) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (k) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. Eilitz, U.; Lessmann, F.; Seidelmann, O.; Wendisch, V. Tetrahedron: Asymmetry 2003, 14, 189-191.
13. For related reviews, see: (a) Krause, N.; Hoffmann-Roder, A. Synlett 2001, 171-196. (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 224-258. For representative recent reports, see: (d) Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (e) Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79-80. (f) Versleijen, J. P. G.; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (g) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778. (h) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700-3701. (i) Ongeri, S.; Piarulli, U.; Jackson, R. F. W.; Gennari, C. Eur. J. Org. Chem. 2001, 803-807. (j) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (k) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. Eilitz, U.; Lessmann, F.; Seidelmann, O.; Wendisch, V. Tetrahedron: Asymmetry 2003, 14, 189-191.
14. For related reviews, see: (a) Krause, N.; Hoffmann-Roder, A. Synlett 2001, 171-196. (b) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (c) Feringa, B. L.; Naasz, R.; Imbos, R.; Arnold, L. A. In Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, 2002; pp 224-258. For representative recent reports, see: (d) Sewald, N.; Wendisch, V. Tetrahedron: Asymmetry 1998, 9, 1341-1344. (e) Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79-80. (f) Versleijen, J. P. G.; van Leusen, A. M.; Feringa, B. L. Tetrahedron Lett. 1999, 40, 5803-5806. (g) Duursma, A.; Minnaard, A. J.; Feringa, B. L. Tetrahedron 2002, 58, 5773-5778. (h) Duursma, A.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2003, 125, 3700-3701. (i) Ongeri, S.; Piarulli, U.; Jackson, R. F. W.; Gennari, C. Eur. J. Org. Chem. 2001, 803-807. (j) Alexakis, A.; Benhaim, C. Org. Lett. 2000, 2, 2579-2581. (k) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. Eilitz, U.; Lessmann, F.; Seidelmann, O.; Wendisch, V. Tetrahedron: Asymmetry 2003, 14, 189-191.
15. Luchaco-Cullis, C. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 8192-8193. Also see ref 2k for related examples.
16. For Rh-catalyzed conjugate additions of arylboronic acids to nitroalkenes, see: (a) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (b) Hayashi, T. Synlett 2001, 171-196.
17. For Rh-catalyzed conjugate additions of arylboronic acids to nitroalkenes, see: (a) Hayashi, T.; Senda, T.; Ogasawara, M. J. Am. Chem. Soc. 2000, 122, 10716-10717. (b) Hayashi, T. Synlett 2001, 171-196.
18. 2Zn as the alkylating agent, enantioselectivities >80% ee have been reported (R = Cy, 96% ee and R = Ph, 84% ee). See ref 2g,h.
19. Czekelius, C.; Carreira, E. M. Angew. Chem., Int. Ed. 2003, 42, 4793-4795.
20. For other Cu-catalyzed ACA of alkylzincs to unsaturated carbonyls promoted by related amino acid-based chiral phosphines, see: (a) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (b) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781. (c) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363. (d) Hird, A. W.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 1276-1279. (e) Cesati, R. R., III; de Armas, J.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 96-101.
21. For other Cu-catalyzed ACA of alkylzincs to unsaturated carbonyls promoted by related amino acid-based chiral phosphines, see: (a) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (b) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781. (c) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363. (d) Hird, A. W.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 1276-1279. (e) Cesati, R. R., III; de Armas, J.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 96-101.
22. For other Cu-catalyzed ACA of alkylzincs to unsaturated carbonyls promoted by related amino acid-based chiral phosphines, see: (a) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (b) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781. (c) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363. (d) Hird, A. W.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 1276-1279. (e) Cesati, R. R., III; de Armas, J.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 96-101.
23. For other Cu-catalyzed ACA of alkylzincs to unsaturated carbonyls promoted by related amino acid-based chiral phosphines, see: (a) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (b) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781. (c) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363. (d) Hird, A. W.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 1276-1279. (e) Cesati, R. R., III; de Armas, J.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 96-101.
24. For other Cu-catalyzed ACA of alkylzincs to unsaturated carbonyls promoted by related amino acid-based chiral phosphines, see: (a) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (b) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781. (c) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363. (d) Hird, A. W.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 1276-1279. (e) Cesati, R. R., III; de Armas, J.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 96-101.
25. For screening strategies and significant attributes of the amino acid based ligands, see: Hoveyda, A. H. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, 2002; pp 991-1016.
26. Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 4018-4019 and references therein.
27. For example, see: (a) Reference 7d. (b) Murphy, K. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 4690-4691.