Mild and expedient asymmetric reductions of α,β-unsaturated alkenyl and alkynyl ketones by TarB-NO2 and mechanistic investigations of ketone reduction

Journal of Organic Chemistry

Volumn 75, Issue 22, 2010, Pages 7717-7725

  Eagon, Scott ^a   Delieto, Cassandra ^a   McDonald, William J ^a   Haddenham, Dustin ^a   Saavedra, Jaime ^a   Kim, Jinsoo ^a   Singaram, Bakthan ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL; ALKYNYLS; ALLYLIC ALCOHOL; ASYMMETRIC REDUCTION; CYCLOALKENONES; ENANTIOMERIC EXCESS; ENANTIOMERIC PURITY; KETONE REDUCTION; MECHANISTIC STUDIES; OPTIMIZED CONDITIONS; PROPARGYL; PROPARGYL ALCOHOL; TARTARIC ACIDS; TRANSITION STATE;

ACIDS; AROMATIC COMPOUNDS; ENANTIOMERS; ENANTIOSELECTIVITY; KETONES; OPTIMIZATION;

REDUCTION;

2 CYCLOHEXENONE; ACETOPHENONE; ALCOHOL DERIVATIVE; ALIPHATIC KETONE; ALLYL ALCOHOL; AROMATIC COMPOUND; BORONIC ACID DERIVATIVE; KETONE DERIVATIVE; SODIUM BOROHYDRIDE; TARTARIC ACID;

ARTICLE; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; MOLECULAR INTERACTION; REACTION OPTIMIZATION; REDUCTION; TEMPERATURE;

EID: 78449265213     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101530f     Document Type: Article

References (58)

1. Luche, J. J. Am. Chem. Soc. 1978, 100, 2226
2. Pragani, R.; Roush, W. Org. Lett. 2008, 70, 4613
3. Gollner, A.; Mulzer, J. Org. Lett. 2008, 70, 4701
4. Westermann, J.; Schneider, M.; Platzek, J.; Petrov, O. Org. Process Res. Dev. 2007, 11, 200
5. Tsegay, S.; Huegal, H.; Rizzacasa, M. Aust. J. Chem. 2009, 62, 676
6. Taber, D.; Gu, P.; Li, R. J. Org. Chem. 2009, 74, 5516
7. Van Innis, L.; Plancher, J.; Marko, I. Org. Lett. 2006, 8, 6111
8. Hannedouche, J.; Kenny, J.; Walsgrove, T.; Wills, M. Synlett 2002, 263
9. Peach, P.; Cross, D.; Kenny, J.; Mann, I.; Houson, I.; Campbell, L; Walsgrove, T.; Wills, M. Tetrahedron 2006, 62, 1864
10. Musa, M.; Ziegelmann-Fjeld, K.; Vieille, C.; Zeikus, J.; Phillips, R. J. Org. Chem. 2007, 72, 30
11. Polland, D; Telari, K.; Lane, J.; Humphrey, G.; McWilliams, C.; Nidositko, S.; Salmon, P.; Moore, J. Biotechnol. Bioeng. 2006, 93, 674
12. Zagozda, M.; Plenkiewicz, J. Tetrahedron: Asymmetry 2006, 17, 1958
13. Lovchik, M.; Goeke, A.; Frater, G. J. Org. Chem. 2007, 72, 2427
14. Corey, E. J.; Bakshi, R.; Shibata, S.; Chen, C.; Singh, V. J. Am. Chem. Soc. 1987, 109, 7925
15. Cho, B. T. Tetrahedron 2006, 62, 7621
16. Holub, N.; Neidhofer, J.; Blechert, S. Org. Lett. 2007, 9, 513
17. Kita, Y.; Futamura, J.; Ohba, Y.; Sawama, Y.; Ganesh, J.; Fujioka, H. J. Org. Chem. 2003, 68, 5917
18. Midland, M.; Tramontano, A.; Kazubski, A.; Graham, R.; Tsai, D.; Cardin, D. Tetrahedron 1984, 40, 1371
19. Gopalsamuthriam, V.; Predeus, A.; Huang, R.; Wulff, R. J. Am. Chem. Soc. 2009, 131, 18018
20. Desrat, S.; Weghe, P. J. Org. Chem. 2009, 74, 6728
21. Cho, B.; Park, W. Bull. Korean Chem. Soc. 1987, 8, 257
22. Morris, D.; Hayes, A.; Wills, M. J. Org. Chem. 2006, 71, 7035
23. Tanaka, K.; Shoji, T. Org. Lett. 2005, 7, 3561
24. Ford, A.; Woodward, S. Angew. Chem., Int. Ed. 1999, 38, 335
25. Blake, A.; Cunningham, A.; Ford, A.; Teat, S.; Woodward, S. Chem.-Eur. J. 2000, 6, 3586
26. Schubert, T.; Hummel, W.; Kula, M.; Muller, M. Eur. J. Org. Chem. 2001, 4181
27. Ohkuma, T.; Ikehira, H.; Ikaria, T.; Noyori, R. Synlett 1997, 467
28. Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417
29. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738
30. Yu, B.; Jiang, T.; Quan, W.; Li, J.; Pan., X.; She, X. Org. Lett. 2009, 11, 629
31. Ferrer, E.; Alibes, R.; Busque, F.; Figueredo, M.; Font, J.; de March, P. J. Org. Chem. 2009, 74, 2425
32. Takamura, H.; Kadonaga, H.; Yamano, Y.; Han, C.; Kadota, I.; Uemura, D. Tetrahedron 2009, 65, 7449
33. Paterson, I.; Burton, P.; Cordier, C.; Housden, M.; Muhlthan, F.; Loiseleur, O. Org. Lett. 2009, 11, 693
34. Smith, A.; Sfouggatakis, C.; Risatti, C.; Sperry, J.; Zhu, W.; Doughty, V.; Tomoika, T.; Gotchev, D.; Bennett, C.; Sakamoto, S.; Atasoylu, O.; Shohei, S.; Bauer, D.; Takeuchi, M.; Makoto, J.; Sakamoto, Y. Tetrahedron 2009, 65, 6489
35. Kim, M.; Kim, H.; Tae, J. Synlett 2009, 8, 1303
36. Georges, Y.; Ariza, X.; Garcia, J. J. Org. Chem. 2009, 74, 2008
37. Kleinbeck, F.; Carriera, E. Angew. Chem., Int. Ed. 2009, 48, 578
38. Yadav, J.; Premalatha, K.; Harshavardhan, S.; Subba Reddy, B. Tetrahedron Lett. 2008, 49, 6765
39. Gais, H.; Kramp, G.; Wolters, D.; Reddy, L. Chem.-Eur. J. 2006, 12, 5610
40. Skuballa, W.; Schillinger, E.; Sturzebecher, C.; Vorbruggen, H. J. Med. Chem. 1986, 29, 313
41. Davies, J.; Wang, H.; Taylor, T.; Warabi, K.; Huang, X. Org. Lett. 2005, 7, 5233
42. Kim, J.; Brunigh, J.; Park, K.; Lee, D.; Singaram, B. Org. Lett. 2009, 11, 4358
43. Eagon, S. C.; Kim, J.; Yan, K.; Haddenham, D.; Singaram, B. Tetrahedron Lett. 2007, 48, 9025
44. Eagon, S. C.; Kim, J.; Singaram, B. Synthesis 2008, 23, 3874
45. Kowalski, C. J.; Weber, A. E.; Fields, K. W. J. Org. Chem. 1982, 47, 5088
46. Krafft, M. E.; Cran, J. W. Synlett 2005, 1263
47. Felpin, F. X. J. Org. Chem. 2005, 70, 8575
48. Brown, H. C.; Ramachandran, V. Acc. Chem. Res. 1992, 25, 16
49. Helal, C.; Magriotis, P.; Corey, E. J. Am. Chem. Soc. 1996, 118, 10938
50. Brown, H. C.; Pai, G. J. Org. Chem. 1985, 50, 1384
51. Cordes, D.; Nguyen, T.; Kwong, T.; Suri, J.; Luibrand, R.; Singaram, B. Eur. J. Org. Chem. 2005, 5289
52. Swager, T. M.; Song, C. Org. Lett. 2008, 10, 3575
53. Martin, R. B. Chem. Rev. 1996, 96, 3043
54. Note that the alkyne group has a higher priority than the tert -butyl group under the Cahn-Ingold-Prelog convention.
55. Schmidt, M.; Baldridge, K.; Boatz, A.; Elbert, S.; Gordon, M.; Jensen, J.; Koseki, S.; Matsunaga, N.; Nguyen, K.; Windus, T.; Dupuis, M.; Montgomery, J., Jr. J. Comput. Chem. 1993, 14, 1347
56. Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158
57. Hehre, W.; Ditchfield, R.; Pople, J. J. Chem. Phys. 1972, 56, 2257
58. Frish, M.; Pople, J.; Binkley, J. J. Chem. Phys. 1984, 80, 3265