Enantioselective Cu-catalyzed conjugate addition of diethylzinc to acyclic aliphatic enones

Organic Letters

Volumn 6, Issue 22, 2004, Pages 4117-4119

  Duncan, Andrew P ^a   Leighton, James L ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC COMPOUND; ZINC DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHIRALITY; CONJUGATION; ENANTIOSELECTIVITY; ENVIRONMENTAL TEMPERATURE;

CATALYSIS; COPPER; KETONES; LIGANDS; MODELS, CHEMICAL; ORGANOMETALLIC COMPOUNDS; PHOSPHINES; STEREOISOMERISM; SULFONAMIDES; TEMPERATURE;

EID: 8744264050     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048191o     Document Type: Article

References (21)

1. For recent reviews, see: (a) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (b) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196. (c) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353.
2. For recent reviews, see: (a) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (b) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196. (c) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353.
3. For recent reviews, see: (a) Alexakis, A.; Benhaim, C. Eur. J. Org. Chem. 2002, 3221-3236. (b) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171-196. (c) Feringa, B. L. Acc. Chem. Res. 2000, 33, 346-353.
4. See ref 1 and (a) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (b) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (c) Liang, L.; Au-Yeung, T. T.-L.; Chan, A. S. C. Org. Lett. 2002, 4, 3799-3801. (d) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363.
5. See ref 1 and (a) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (b) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (c) Liang, L.; Au-Yeung, T. T.-L.; Chan, A. S. C. Org. Lett. 2002, 4, 3799-3801. (d) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363.
6. See ref 1 and (a) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (b) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (c) Liang, L.; Au-Yeung, T. T.-L.; Chan, A. S. C. Org. Lett. 2002, 4, 3799-3801. (d) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363.
7. See ref 1 and (a) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756. (b) Alexakis, A.; Benhaim, C.; Rosset, S.; Humam, M. J. Am. Chem. Soc. 2002, 124, 5262-5263. (c) Liang, L.; Au-Yeung, T. T.-L.; Chan, A. S. C. Org. Lett. 2002, 4, 3799-3801. (d) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 13362-13363.
8. (a) Hu, X.; Chen, H.; Zhang, X. Angew. Chem., Int. Ed. 1999, 38, 3518-3521.
9. (b) Shintani, R.; Fu, G. C. Org. Lett. 2002, 4, 3699-3702.
10. (c) Hu, Y.; Liang, X.; Wang, J.; Zheng, Z.; Hu, X. Tetrahedron: Asymmetry 2003, 14, 3907-3915.
11. (d) Morimoto, T.; Mochizuki, N.; Suzuki, M. Tetrahedron Lett. 2004, 45, 5717-5722.
12. (a) Alexakis, A.; Rosset, S.; Allamand, J.; March, S.; Guillen, F.; Benhaim, C. Synlett 2001, 1375-1378.
13. (b) Alexakis, A.; Polet, D.; Rosset, S.; March, S. J. Org. Chem. 2004, 69, 5660-5667.
14. Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779-781.
15. Krauss, I. J.; Leighton, J. L. Org. Lett. 2003, 5, 3201-3203.
16. This is a new ligand class. For related [NPN] ligands, see: (a) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 6565-6568. (b) Schrock, R. R.; Seidel, S. W.; Schrodi, Y.; Davis, W. M. Organometallics 1999, 18, 428-437. (c) Fryzuk, M. D.; Johnson, S. A.; Rettig, S. J. J. Am. Chem. Soc. 1998, 120, 11024-11025.
17. This is a new ligand class. For related [NPN] ligands, see: (a) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 6565-6568. (b) Schrock, R. R.; Seidel, S. W.; Schrodi, Y.; Davis, W. M. Organometallics 1999, 18, 428-437. (c) Fryzuk, M. D.; Johnson, S. A.; Rettig, S. J. J. Am. Chem. Soc. 1998, 120, 11024-11025.
18. This is a new ligand class. For related [NPN] ligands, see: (a) Jiang, Y.; Jiang, Q.; Zhu, G.; Zhang, X. Tetrahedron Lett. 1997, 38, 6565-6568. (b) Schrock, R. R.; Seidel, S. W.; Schrodi, Y.; Davis, W. M. Organometallics 1999, 18, 428-437. (c) Fryzuk, M. D.; Johnson, S. A.; Rettig, S. J. J. Am. Chem. Soc. 1998, 120, 11024-11025.
19. Cernerud, M.; Skrinning, A.; Bergère, I.; Moberg, C. Tetrahedron: Asymmetry 1997, 8, 3437-3441.
20. An X-ray crystallographic study of the minor diastereomer allowed the assignment of relative configuration for 4a and 4b. See Supporting Information.
21. During the course of this work, Nelson reported the synthesis of an amino bis(sulfonamide) ligand bearing identical differential substitution on the two sulfonamide arms: Nelson, S. G.; Zhu, C.; Shen, X. J. Am. Chem. Soc. 2004, 126, 14-15.