Asymmetric reduction of aliphatic ketones and acyl silanes using chiral anti-pentane-2,4-diol and a catalytic amount of 2,4-dinitrobenzenesulfonic acid

Tetrahedron

Volumn 66, Issue 32, 2010, Pages 6062-6069

  Matsuo, Jun Ichi ^a   Hattori, Yu ^a   Hashizume, Mio ^a   Ishibashi, Hiroyuki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Acyl silane; Asymmetric reduction; Ketone; Meerwein Ponndorf Verley reduction; Oppenauer oxidation

Indexed keywords

2,4 DINITROBENZENESULFONIC ACID; ALCOHOL DERIVATIVE; ALIPHATIC KETONE; ANTIPENTANE 2,4 DIOL; BENZENE; BRONSTED ACID; SILANE DERIVATIVE; SULFONIC ACID DERIVATIVE; THIOL; UNCLASSIFIED DRUG;

ACETALIZATION; ARTICLE; CATALYSIS; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SOLVENT EFFECT;

EID: 77955416348     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.06.012     Document Type: Article

References (61)

1. A.L. Wilds Org. React. 2 1944 178
2. C.F. de Graauw, J.A. Peters, H. van Bekkum, and J. Huskens Synthesis 1994 1007
3. R. Kow, R. Nygren, and M.W. Rathke J. Org. Chem. 42 1977 826
4. K.G. Akamanchi, and N.R. Varalakshmy Tetrahedron Lett. 36 1995 3571
5. T. Ooi, T. Miura, and K. Maruoka Angew. Chem., Int. Ed. 37 1998 2347
6. E.J. Campbell, H. Zhou, and S.T. Nguyen Org. Lett. 3 2001 2391
7. T. Ooi, Y. Itagaki, T. Miura, and K. Maruoka Tetrahedron Lett. 40 1999 2137
8. G. Gal, and I. Krasznai Magy. Kem. Foly. 62 1956 155
9. G. Gal, and E. Krasznai Acta Chim. Acad. Sci. Hung. 17 1958 171
10. B.-T. Ko, C.-C. Wu, and C.-C. Lin Organometallics 19 2000 1864
11. K. Konishi, K. Makita, T. Aida, and S. Inoue J. Chem. Soc., Chem. Commun. 1988 643
12. J.L. Namy, J. Souppe, J. Collin, and H.B. Kagan J. Org. Chem. 49 1984 2045
13. A. Lebrun, J.L. Namy, and H.B. Kagan Tetrahedron Lett. 32 1991 2355
14. Asymmetric catalysis (a) D.A. Evans, S.G. Nelson, M.R. Gagne, and A.R. Muci J. Am. Chem. Soc. 115 1993 9800
15. E.J. Campbell, H. Zhou, and T. Nguyen SonBinh Angew. Chem., Int. Ed. 41 2002 1020
16. J. Matsuo, Y. Hattori, and H. Ishibashi Org. Lett. 12 2010 2294
17. J. Matsuo, T. Kozai, O. Nishikawa, Y. Hattori, and H. Ishibashi J. Org. Chem. 73 2008 6902
18. A. Mori, J. Fujiwara, K. Maruoka, and H. Yamamoto Tetrahedron Lett. 24 1983 4581
19. A. Mori, J. Fujiwara, K. Maruoka, and H. Yamamoto J. Organomet. Chem. 285 1985 83
20. W.G. Dauben, J.M. Gerdes, and G.C. Look J. Org. Chem. 51 1986 4964
21. E.J. Corey, and C.J. Helal Angew. Chem., Int. Ed. 37 1998 1986
22. S. Itsuno Org. React. 52 1998 395
23. H. Dong, H. Du, S.R. Wickramasinghe, and X. Qian J. Phys. Chem. B 113 2009 14094
24. D.S. Crumrine, J.M. Shankweiler, and R.V. Hoffman J. Org. Chem. 51 1986 5013
25. M. Bos, and E.A.M.F. Dahmen Anal. Chim. Acta 57 1971 361
26. Acetal 24 was not detected in DNBSA-catalyzed reduction of ketones with anti-1,3-diols 15. On the other hand, syn-1,3-diol 11 gave the corresponding acetal 16 which has two methyl groups both in equatorial positions (Table 4, entry 4).
27. K. Ishihara, N. Hanaki, and H. Yamamoto J. Am. Chem. Soc. 113 1991 7074
28. K. Ishihara, N. Hanaki, and H. Yamamoto Synlett 1993 127
29. K. Ishihara, N. Hanaki, and H. Yamamoto J. Am. Chem. Soc. 115 1993 10695
30. P.E. Shaw J. Org. Chem. 31 1966 2116
31. O.R. Martin, S.P. Rao, H.A. El-Shenawy, K.G. Kurz, and A.B. Cutler J. Org. Chem. 53 1988 3287
32. C. Djerassi Org. React. 6 1951 207
33. Allylic alcohol formed by reduction of 26 was not obtained, probably because dehydration of the allylic alcohol took place.
34. I. Fleming, A. Barbero, and D. Walter Chem. Rev. 97 1997 2063
35. J.R. Huckins, and S.D. Rychnovsky J. Org. Chem. 68 2003 10135
36. J.D. Buynak, J.B. Strickland, G.W. Lamb, D. Khasnis, S. Modi, D. Williams, and H. Zhang J. Org. Chem. 56 1991 7076
37. J.D. Buynak, J.B. Strickland, T. Hurd, and A. Phan J. Chem. Soc., Chem. Commun. 1989 89
38. J.A. Soderquist, C.L. Anderson, E.I. Miranda, I. Rivera, and G.W. Kabalka Tetrahedron Lett. 31 1990 4677
39. K. Takeda, Y. Ohnishi, and T. Koizumi Org. Lett. 1 1999 237
40. N. Arai, K. Suzuki, S. Sugizaki, H. Sorimachi, and T. Ohkuma Angew. Chem., Int. Ed. 47 2008 1770
41. A. Ricci, and A. Degl'Innocenti Synthesis 1989 647
42. B.F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti, and A. Ricci J. Organomet. Chem. 567 1998 181
43. P.F. Cirillo, and J.S. Panek Org. Prep. Proced. Int. 24 1992 553
44. B.F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti, F. Peri, and A. Ricci J. Chem. Soc., Perkin Trans. 1 1996 2803
45. H. Bock, H. Alt, and H. Seidl J. Am. Chem. Soc. 91 1969 355
46. J. Yoshida, M. Itoh, S. Matsunaga, and S. Isoe J. Org. Chem. 57 1992 4877
47. S.D. Rychnovsky, G. Griesgraber, S. Zeller, and D.J. Skalitzky J. Org. Chem. 56 1991 5161
48. A. Guijarro, and M. Yus Tetrahedron 52 1996 1797
49. R. Todesco, D.V. Bockstaele, J. Gelan, H. Martens, J. Put, and F.C. De Schryver J. Org. Chem. 48 1983 4963
50. H.J. Reich, E.K. Eisenhart, R.E. Olson, and M.J. Kelly J. Am. Chem. Soc. 108 1986 7791
51. K. Yamamoto, A. Hayashi, S. Suzuki, and J. Tsuji Organometallics 6 1987 974
52. J. Enda, and I. Kuwajima J. Am. Chem. Soc. 107 1985 5495
53. C.T. Clark, B.C. Milgram, and K.A. Scheidt Org. Lett. 6 2004 3977
54. P. Doussot, and C. Portella J. Org. Chem. 58 1993 6675
55. J. Cossrow, and S.D. Rychnovsky Org. Lett. 4 2002 147
56. I. Ohtani, T. Kusumi, Y. Kashman, and H. Kakisawa J. Am. Chem. Soc. 113 1991 4092
57. P.G. Cozzi, and P. Kotrusz J. Am. Chem. Soc. 128 2006 4940
58. S. Eagon, J. Kim, K. Yan, D. Haddenham, and B. Singaram Tetrahedron Lett. 48 2007 9025
59. W.K. Yang, and B.T. Cho Tetrahedron: Asymmetry 11 2000 2947
60. K. Shimoda, N. Kubota, H. Hamada, S.Y. Yamane, and T. Hirata Bull. Chem. Soc. Jpn. 77 2004 2269
61. Y.S. Sokeirik, H. Mori, M. Omote, K. Sato, A. Tarui, I. Kumadaki, and A. Ando Org. Lett. 9 2007 1927