Influence of α-methyl substitution of proline-based organocatalysts on the asymmetric α-oxidation of aldehydes

Tetrahedron

Volumn 65, Issue 25, 2009, Pages 4801-4807

 

^a Amy)   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; METHYL GROUP; NITROSOBENZENE; OXAZIRIDINE DERIVATIVE; PROLINE; TETRAZOLE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CONTROLLED STUDY; ENANTIOSELECTIVITY; ISOMER; OXIDATION; PRIORITY JOURNAL; STATISTICAL SIGNIFICANCE; SUBSTITUTION REACTION;

EID: 65549139247     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.04.060     Document Type: Article

References (61)

1. Bogevig A., Sunden H., and Cordova A. Angew. Chem. 43 (2004) 1109-1112
2. Hayashi Y., Yamaguchi J., Sumiya T., and Shoji M. Angew. Chem. 43 (2004) 1112-1115
3. Review:. Davis F.A., and Chen B.C. Chem. Rev. 92 (1992) 919-934 and references therein
4. Enders D., and Bhushan V. Tetrahedron Lett. 29 (1988) 2437-2440
5. Lohray B.B., and Enders D. Helv. Chim. Acta 72 (1989) 980-984
6. Enders D., and Reinhold U. Synlett (1994) 792-794
7. Enders D., and Reinhold U. Liebigs Ann. (1996) 11-26
8. Enders D., and Bockstiegel B. Synthesis (1989) 493-496
9. Morikawa K., Park J., Andersson P.G., Hashiyama T., and Sharpless K.B. J. Am. Chem. Soc. 115 (1993) 8463-8464
10. Hashiyama T., Morikawa K., and Sharpless K.B. J. Org. Chem. 57 (1992) 5067-5068 For a Sharpless epoxidation route, see:
11. Paju A., Kanger T., Pehk T., and Lopp M. Tetrahedron: Asymmetry 58 (2002) 7321-7326
12. Zhu Y., Yu Y., Yu H., and Shi Y. Tetrahedron Lett. 39 (1998) 7819-7822
13. Adam W., Fell R.T., Saha-Moller C.R., and Zhao C.-G. Tetrahedron: Asymmetry 9 (1998) 397-401
14. Adam W., Fell R.T., Stegmann V.R., and Saha-Moller C.R. J. Am. Chem. Soc. 120 (1998) 708-714
15. Adam W., Fell R.T., Mock-Knoblauch C., and Saja-Moller C.R. Tetrahedron Lett. 37 (1996) 6531-6534
16. Fukuda T., and Katsuki T. Tetrahedron Lett. 37 (1996) 4389-4392
17. Reddy D.R., and Thornton E.R. J. Chem. Soc., Chem. Commun. (1992) 172-173
18. Momiyama N., and Yamamoto H. J. Am. Chem. Soc. 125 (2003) 6038-6039
19. Morales M.R., Momiyama N., and Yamamoto H. Synlett (2006) 705-708
20. Zhong G. Angew. Chem. 42 (2003) 4247-4250
21. Hayashi Y., Yamaguchi J., Hibino K., and Shoji M. Tetrahedron Lett. 44 (2003) 8293-8396
22. Hayashi Y., Yamaguchi J., Sumiya T., Hibino K., and Shoji M. J. Org. Chem. 69 (2004) 5966-5973
23. Brown S.P., Brochu M.P., Christopher J.S., and MacMillan D.W.C. J. Am. Chem. Soc. 125 (2003) 10808-10809
24. Momiyama N., Torii H., Saito S., and Yamamoto H. Proc. Natl. Acad. Sci. U.S.A. 101 (2004) 5374-5378
25. Engqvist M., Casas J., Sunden H., Ibrahem I., and Cordova A. Tetrahedron Lett. 46 (2005) 2053-2057
26. Tong S.-T.A., Harris P.W.R., Barker D., and Brimble M.A. Eur. J. Org. Chem. (2008) 164-170
27. Davis F.A., Lamendola Jr. J., Nadir U., Kluger E.W., Sedergran T.C., Panunto T.W., Billmers R., Jenkins Jr. R., Turchi I.J., Watson W.H., Chen J.S., and Kimura M. J. Am. Chem. Soc. 102 (1980) 2000-2005
28. García Ruano J.L., Alemán J., Fajardo C., and Parra A. Org. Lett. 7 (2005) 5493-5496
29. Forte M., Orsini F., and Pelizzoni F. Gazz. Chim. Ital. 115 (1985) 569-571
30. Fujisawa H., Takahashi E., and Mukaiyama T. Chem.-Eur. J. 12 (2006) 5082-5093
31. 3S requires 358.14769.
32. 16 stated that sulfonimine was resistant to hydrolysis, our results suggested that in the presence of proline, sulfonimine 8 underwent hydrolysis readily.
33. Caputo R., Cecere G., Guaragna A., Palumbo G., and Pedatella S. Eur. J. Org. Chem. (2002) 3050-3054
34. Cordova A., Sunden H., Engqvist M., Ibrahem I., and Casas J. J. Am. Chem. Soc. 126 (2004) 8914-8915
35. Ketone 10 was synthesized from the condensation of cyclohexanone and benzaldehyde followed by dehydration with conc. HCl, according to known procedures:. Peijnenburg W.J.G.M., and Buck H.M. Tetrahedron 44 (1988) 4927-4940
36. Sunden H., Engqvist J., Casas J., Ibrahem I., and Cordova A. Angew. Chem., Int. Ed. 43 (2004) 6532-6535
37. List B., Pojarliev P., Biller W.T., and Martin H.J. J. Am. Chem. Soc. 124 (2002) 827-833
38. Hayashi Y., Tsuboi W., Ashimine I., Urushmia T., Shoji M., and Sakai K. Angew. Chem., Int. Ed. 42 (2003) 3677-3680
39. Cordova A. Synlett (2003) 1651-1654
40. Cordova A., Notz W., Zhong G., Betancort J., and Barbas III C.F. J. Am. Chem. Soc. 124 (2002) 1842-1843
41. Cordova A., Watanabe S., Tanaka F., Notz W., and Barbas III C.F. J. Am. Chem. Soc. 124 (2002) 1866-1867
42. List B. J. Am. Chem. Soc. 122 (2000) 9336-9337
43. Mioskowski, C.; Wagner, A.; Catala, C. Fr. Demande Patent 2854629, 2004.
44. Winfield C.J., Al-Mahrizy Z., Gravestock M., and Bugg T.D.H. J. Chem. Soc., Perkin Trans. 1 (2000) 3277-3289
45. Ohta T., Hosoi A., and Nozoe S. Tetrahedron Lett. 29 (1988) 329-332
46. Caputo R., Cecere G., Guaragna A., Palumbo G., and Pedatella S. Eur. J. Org. Chem. (2002) 3050-3054
47. Carson C.A., and Kerr M.A. Angew. Chem., Int. Ed. 45 (2006) 6560-6563
48. Kaliappan K.P., and Gowrisankar P. Synlett (2007) 1537-1540
49. Evans D.A., Morrissey M.M., and Dorow R.L. J. Am. Chem. Soc. 107 (1985) 4346-4348
50. Fu A., List B., and Thiel W. J. Org. Chem. 71 (2006) 320-326
51. Bahmanyar S., and Houk K.N. J. Am. Chem. Soc. 123 (2001) 12911-12912
52. Cheong P.H.-Y., Houk K.N., Warrier J.S., and Hanessian S. Adv. Synth. Catal. 346 (2004) 1111-1115
53. Whilst the syn enamine is favoured over the anti in the density functional study on the alkylation reaction, upon inclusion of trimethylamine, which supposedly plays a crucial role in the reaction, the calculation has then demonstrated superiority of the anti over the syn. See Ref. 28.
54. α,α-Disubstituted α-amino acids have been found to influence the conformation of peptides into which they are inserted:. Zhuang W., Saaby S., and Jorgensen K.A. Angew. Chem., Int. Ed. 43 (2004) 4476-4478 and references therein
55. Tong S.-T., Barker D., Choi K.W., Boyd P.D.W., and Brimble M.A. Acta Crystallogr., Sect. E: Struct. Rep. Online 64 (2008) 2174-2174
56. Córdova A., Sundén H., Bøgevig A., Johansson M., and Himo F. Chem.-Eur. J. 10 (2004) 3673-3684
57. Nicolaou K.C., Snyder S.A., Longbottom D.A., Nalbandian A.Z., and Huang X. Chem.-Eur. J. 10 (2004) 5581-5606
58. Moreno-Dorado F.J., Guerra F.M., Ortega M.J., Zubía E., and Massanet G.M. Tetrahedron: Asymmetry 14 (2003) 503-510
59. Davies S.G., Key M.-S., Rodriguez-Solla H., Sanganee H., Savory E.D., and Smith A.D. Synlett (2003) 1659-1662
60. Li Y., Song D., and Dong V.M. J. Am. Chem. Soc. 130 (2008) 2962-2964
61. Tong S.-T., Barker D., Choi K.W., Boyd P.D.W., and Brimble M.A. Acta Crystallogr., Sect. E: Struct. Rep. Online 64 (2008) 1990-1990