Enantioselective hydroformylation of N-vinyl carboxamides, allyl carbamates, and allyl ethers using chiral diazaphospholane ligands

Journal of the American Chemical Society

Volumn 132, Issue 40, 2010, Pages 14027-14029

  McDonald, Richard I ^a   Wong, Gene W ^a   Neupane, Ram P ^a   Stahl, Shannon S ^a   Landis, Clark R ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ETHERS; ASYMMETRIC HYDROFORMYLATION; BENZYL ETHERS; CARBOXAMIDES; CATALYST LOADINGS; CHIRAL ALDEHYDE; ENANTIOSELECTIVE; HIGH ENANTIOSELECTIVITY; RHODIUM COMPLEXES; SHORT REACTION TIME; SILYL ETHERS;

ALDEHYDES; AMINES; ENANTIOSELECTIVITY; ETHERS; GLASS BOTTLES; HYDROFORMYLATION; LIGANDS; OLEFINS; PALLADIUM; RHODIUM; RHODIUM COMPOUNDS;

HYDROXYLATION;

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; ALLYL COMPOUND; AMIDE; BENZYL DERIVATIVE; CARBAMIC ACID DERIVATIVE; ETHER DERIVATIVE; HETEROCYCLIC COMPOUND; LIGAND; PALLADIUM; PHOSPHORUS DERIVATIVE; RHODIUM COMPLEX; SILANE DERIVATIVE; VINYL DERIVATIVE;

AMINATION; ARTICLE; BIOTRANSFORMATION; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; HYDROFORMYLATION; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

AMIDES; AZA COMPOUNDS; CARBAMATES; ETHERS; LIGANDS; STEREOISOMERISM;

EID: 77957698321     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja106674n     Document Type: Article

References (39)

1. Rhodium Catalyzed Hydroformylation; Claver, C. and van Leeuwen, P. W. N. M., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2000.
2. Klosin, J. and Landis, C. R. Acc. Chem. Res. 2007, 40, 1251-1259 and references within
3. For recent examples of novel ligands for AHF, see
4. Babin, J. E. and Whiteker, G. T. Patent WO 93/03830, 1992.
5. Breeden, S., Cole-Hamilton, D. J., Foster, D. F., Schwarz, G. J., and Wills, M. Angew. Chem., Int. Ed. 2000, 39, 4106-4108
6. Cobley, C. J., Gardner, K., Klosin, J., Praquin, C., Hill, C., Whiteker, G. T., Zanotti-Gerosa, A., Petersen, J. L., and Abboud, K. A. J. Org. Chem. 2004, 69, 4031-4040
7. Zhao, B., Peng, X., Wang, Z., Xia, C., and Ding, K. Chem.-Eur. J. 2008, 14, 7847-7857
8. Zhang, X., Cao, B., Yan, Y., Yu, S., Ji, B., and Zhang, X. Chem.-Eur. J. 2010, 16, 871-877
9. Clark, T. P., Landis, C. R., Freed, S. L., Klosin, J., and Abboud, K. A. J. Am. Chem. Soc. 2005, 127, 5040-5042
10. Thomas, P. J., Axtell, A. T., Klosin, J., Peng, W., Rand, C. L., Clark, T. P., Landis, C. R., and Abboud, K. A. Org. Lett. 2007, 9, 2665-2668
11. Watkins, A. L., Hashiguchi, B. G., and Landis, C. R. Org. Lett. 2008, 10, 4553-4556
12. Sakai, N., Mano, S., Nozaki, K., and Takaya, H. J. Am. Chem. Soc. 1993, 115, 7033-7034
13. Nozaki, K., Sakai, N., Nanno, T., Higashijima, T., Mano, S., Horiuchi, T., and Takaya, H. J. Am. Chem. Soc. 1997, 119, 4413-4423
14. Horiuchi, T., Ohta, T., Shirakawa, E., Nozaki, K., and Takaya, H. J. Org. Chem. 1997, 62, 4285-4292
15. Horiuchi, T., Shirakawa, E., Nozaki, K., and Takaya, H. Organometallics 1997, 16, 2981-2986
16. Nozaki, K., Li, W., Horiuchi, T., and Takaya, H. Tetrahedron Lett. 1997, 38, 4611-4614
17. Nozaki, K., Matsuo, T., Shibahara, F., and Hiyama, T. Adv. Synth. Catal. 2001, 343, 61-63
18. Shibahara, F., Nozaki, K., and Hiyama, T. J. Am. Chem. Soc. 2003, 125, 8555-8560
19. For additional important reports of the AHF of related substrates, see
20. Becker, Y., Eisenstadt, A., and Stille, J. K. J. Org. Chem. 1980, 45, 2145-2151
21. Parrinello, G., Deschenaux, R., and Stille, J. K. J. Org. Chem. 1986, 51, 4189-4195
22. Parrinello, G. and Stille, J. K. J. Am. Chem. Soc. 1987, 109, 7122-7127
23. Gladiali, S. and Pinna, L. Tetrahedron: Asymmetry 1990, 1, 693-696
24. Gladiali, S. and Pinna, L. Tetrahedron: Asymmetry 1991, 2, 623-632
25. Zhang, X., Cao, B., Yu, S., and Zhang, X. Angew. Chem., Int. Ed. 2010, 49, 4047-4050
26. 1H NMR spectroscopy.
27. Brice, J. L., Meerdink, J. E., and Stahl, S. S. Org. Lett. 2004, 6, 1845-1848
28. For selected recent examples, see
29. Smith, A. B., III, Beauchamp, T. J., LaMarche, M. J., Kaufman, M. D., Qiu, Y., Arimoto, H., Jones, D. R., and Kobayashi, K. J. Am. Chem. Soc. 2000, 122, 8654-8664
30. Smith, A. B., III, Adams, C. M., Barbosa, S. A. L., and Degnan, A. P. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12042-12047
31. Mickel, S. J., Sedelmeier, G. H., Niederer, D., Schuerch, F., Koch, G., Kuesters, E., Daeffler, R., Osmani, A., Seeger-Weibel, M., Schmid, E., Hirni, A., Schaer, K., Gamboni, R., Bach, A., Chen, S., Chen, W., Geng, P., Jagoe, C. T., Kinder, F. R., Jr., Lee, G. T., McKenna, J., Ramsey, T. M., Repič, O., Rogers, L., Shieh, W.-C., Wang, R.-M., and Waykole, L. Org. Process Res. Dev. 2004, 8, 107-112
32. Lawhorn, B. G., Boga, S. B., Wolkenberg, S. E., Colby, D. A., Gauss, C.-M., Swingle, M. R., Amable, L., Honkanen, R. E., and Boger, D. L. J. Am. Chem. Soc. 2006, 128, 16720-16732
33. 2 (3 μmol), 1 (3 μmol), 80 °C, 5 h. The reaction proceeded with 99% conversion to aldehydes, α:β = 1.8:1, 92% ee. The linear aldehyde can be separated from the branched by flash chromatography to provide the pure chiral aldehyde with no degradation of enantioenrichment.
34. For example, see
35. ref 5c.
36. Sakai, N., Nozaki, K., and Takaya, H. J. Chem. Soc., Chem. Commun. 1994, 395-396
37. Brice, J. L., Harang, J. E., Timokhin, V. I., Anastasi, N. R., and Stahl, S. S. J. Am. Chem. Soc. 2005, 127, 2868-2869
38. AHF of methyl N -acetamidoacrylate has been demonstrated but was shown to provide exclusively the internal regioisomer: see ref 6 d,e.
39. Refer to the Supporting Information for the investigation of additional substrates.