Enantioselective ketone hydroacylation using noyori's transfer hydrogenation catalyst

Journal of the American Chemical Society

Volumn 135, Issue 15, 2013, Pages 5553-5556

  Murphy, Stephen K ^a,b   Dong, Vy M ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC TRANSFER HYDROGENATION; CHEMO-SELECTIVITY; DIRECT PREPARATION; ENANTIOSELECTIVE; HYDROACYLATION; TRANSFER HYDROGENATIONS;

ALDEHYDES; CATALYSTS; HYDROGENATION; KETONES;

ENANTIOSELECTIVITY;

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; KETONE DERIVATIVE; LACTONE DERIVATIVE;

ACYLATION; ARTICLE; CATALYST; CONTROLLED STUDY; ENANTIOSELECTIVITY; HYDROGENATION; NOYORI ASYMMETRIC TRANSFER HYDROGENATION CATALYST; OXIDATION;

ACYLATION; CATALYSIS; HYDROGENATION; KETONES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 84876503610     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4021974     Document Type: Article

References (35)

1. Dictionary of Natural Products. http://dnp.chemnetbase.com (accessed April 3, 2013).
2. Mao, B.; Geurts, K.; Fananas-Mastral, M.; van Zijl, A. W.; Fletcher, S. P.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2011, 13, 948
3. Bandichhor, R.; Nosse, B.; Reiser, O. Top. Curr. Chem. 2005, 243, 43
4. Kitson, R. R. A.; Millemaggi, A.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2009, 48, 9426
5. Shen, Z.; Khan, H. A.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2916
6. Shen, Z.; Dornan, P. K.; Khan, H. A.; Woo, T. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 1077
7. Phan, D. H. T.; Kim, B.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 15608
8. Khan, H. A.; Kou, K. G. M.; Dong, V. M. Chem. Sci 2011, 2, 407
9. Bergens, S. H.; Fairlie, D. P.; Bosnich, B. Organometallics 1990, 9, 566
10. For the use of an NHC to cyclize 2-keto benzaldehydes, see: Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2006, 128, 4558
11. The NHC catalyst from ref 6a was not applicable to the cyclization of 4-oxobutyrophenone. See: Chan, A. Ph.D. Thesis, Northwestern University, Evanston, IL, 2008.
12. 3 gave a 32% yield of the ketone hydroacylation product along with a 55% yield of the aldehyde dimerization product. See: Omura, S.; Fukuyama, T.; Murakami, H. O.; Ryu, I. Chem. Commun. 2009, 6741
13. For the use of iridium hydrides in the hydroacylation of 2-(2-oxopropyl)benzaldehydes, see: Suzuki, T.; Yamada, T.; Watanabe, K.; Katoh, T. Bioorg. Med. Chem. Lett. 2005, 15, 2583
14. Hsu, J.-L.; Fang, J. J. Org. Chem. 2001, 66, 8573
15. Steward, K. M.; Gentry, E. C.; Johnson, J. S. J. Am. Chem. Soc. 2012, 134, 7329
16. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97
17. Dobereiner, G. E.; Crabtree, R. H. Chem. Rev. 2010, 110, 681
18. Shibahara, F.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 14120
19. Williams, V. M.; Leung, J. C.; Patman, R. L.; Krische, M. J. Tetrahedron 2009, 65, 5024
20. Moran, J.; Krische, M. J. Pure Appl. Chem. 2012, 84, 1729
21. Ito, M.; Osaku, A.; Siibashi, A.; Ikariya, T. Org. Lett. 2007, 9, 1821
22. Suzuki, T.; Morita, K.; Tsuchida, M.; Hiroi, K. Org. Lett. 2002, 4, 2361
23. Suzuki, T.; Morita, K.; Matsuo, Y.; Hiroi, K. Tetrahedron Lett. 2003, 44, 2003
24. Endo, Y.; Bäckvall, J.-E. Chem.-Eur. J. 2011, 17, 12596
25. Maytum, H. C.; Tavassoli, B.; Williams, J. M. J. Org. Lett. 2007, 9, 4387
26. Gunanathan, C.; Milstein, D. Acc. Chem. Res. 2011, 44, 588
27. Leung, J. C.; Krische, M. J. Chem. Sci. 2012, 3, 2202
28. Giri, R.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 15860
29. Sewell, L. J.; Lloyd-Jones, G. C.; Weller, A. S. J. Am. Chem. Soc. 2012, 134, 3598
30. Flegeau, F.; Bruneau, C.; Dixneuf, P. H.; Jutand, A. J. Am. Chem. Soc. 2011, 133, 10161
31. For ATH of aryl ketones, see: Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562
32. For ATH of alkynones, see: Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738
33. Yamakawa, M.; Yamada, I.; Noyori, R. Angew. Chem., Int. Ed. 2001, 40, 2818
34. Dub, P. A.; Ikariya, T. J. Am. Chem. Soc. 2013, 135, 2604
35. Bierenstiel, M.; Schlaf, M. Eur. J. Org. Chem. 2004, 1474