A practical synthesis of optically active aromatic epoxides via asymmetric transfer hydrogenation of α-chlorinated ketones with chiral rhodium-diamine catalyst

Tetrahedron

Volumn 60, Issue 34, 2004, Pages 7411-7417

  Hamada, Takayuki ^a   Torii, Takayoshi ^a   Izawa, Kunisuke ^a   Ikariya, Takao ^b  

^a AJINOMOTO CO INC   (Japan)

^b 2 12 1 O okayama M ^*  (Japan)

Author keywords

Chlorinated aromatic ketone; Asymmetric reduction; Optically active epoxide

Indexed keywords

ALCOHOL; DIAMINE; EPOXIDE; FORMIC ACID; HYDROGEN; KETONE DERIVATIVE; RHODIUM; STYRENE OXIDE; TRIETHYLAMINE;

CATALYST; CHIRALITY; CONFERENCE PAPER; ETHERIFICATION; HYDROGENATION; PRIORITY JOURNAL; PURIFICATION; REDUCTION; SYNTHESIS;

EID: 3342948477     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.076     Document Type: Conference Paper

References (54)

1. Uehling D.E., Donaldson K.H., Deaton D.N., Hyman C.E., Sugg E.E., Barrett D.G., Hughes R.G., Reitter B., Adkison K.K., Lancaster M.E., Lee F., Hart H., Paulik M.A., Sherman B.W., True T., Cowman C. J. Med. Chem. 45:2002;567-583
2. CL316243: Bloom J.D., Dutia M.D., Johnson B.D., Wissner A., Burns M.G., Largis E.E., Dolan J.A., Claus T.H. J. Med. Chem. 35:1992;3081-3084
3. SR58611A: Cecchi R., Croci T., Boijegrain R., Boveri S., Baroni M., Boccardi G., Guimbard J.P., Guzzi U. Eur. J. Med. Chem. 29:1994;259-267
4. (d) AJ9677: Kato, S.; Harada, H.; Fujii, A.; Kotai, O. JP 11255743, 1999.
5. (e) Ro40-2148: Alig, L.; Mueller, M. EP 386603, 1991.
6. Palucki M., Pospisil P.J., Zhang W., Jacobsen E.N. J. Am. Chem. Soc. 116:1994;9333-9334
7. Palucki M., McCormick G.J., Jacobsen E.N. Tetrahedron Lett. 36:1995;5457-5460
8. Brandes B.D., Jacobsen E.N. Tetrahedron: Asymmetry. 8:1997;3927-3933
9. Matsuyama, A.; Kobayashi, Y. EP 0611826A2, 1994.
10. Tanaka K., Yasuda M. Tetrahedron: Asymmetry. 9:1998;3275-3282
11. For a review, see: (a) Wallabaum S., Martens J. Tetrahedron: Asymmetry. 3:1992;1475-1504
12. Hett R., Senanayake C.H., Wald S.A. Tetrahedron Lett. 39:1998;1705-1708
13. Yaozhong J., Yong Q., Aiqiao M., Zhitang M. Tetrahedron: Asymmetry. 5:1994;1211-1214
14. (a) Sawa, I.; Konishi, Y.; Maemoto, S.; Hasegawa, J. WO 9201804 A1, 1992.
15. (b) Yasohara, Y., Sawa, I., Ueda, M., Hasegawa, J., Shimizu, A., Kataoka, M., Wada M., Kawabata, J. JP11215995, 1999.
16. Devocelle M., Mortreux A., Agbossou F., Dormoy J.-P. Tetrahedron Lett. 40:1999;4551-4554
17. Murata K., Ikariya T., Noyori R. J. Org. Chem. 64:1999;2186-2187
18. Hashiguchi S., Fujii A., Takehara J., Ikariya T., Noyori R. J. Am. Chem. Soc. 117:1995;7562-7563
19. Fujii A., Hashiguchi S., Uematsu N., Ikariya T., Noyori R. J. Am. Chem. Soc. 118:1996;2521-2522
20. Haack K.-J., Hashiguchi S., Fujii A., Ikariya T., Noyori R. Angew. Chem., Int. Ed. Engl. 36:1997;285-288
21. Hashiguchi S., Fujii A., Haack K.-J., Matsumura K., Ikariya T., Noyori R. Angew. Chem., Int. Ed. Engl. 36:1997;288-290
22. Matsumura K., Hashiguchi S., Ikariya T., Noyori R. J. Am. Chem. Soc. 119:1997;8738-8739
23. Noyori R., Hashiguchi S. Acc. Chem. Res. 30:1997;97-102
24. Hamada T., Torii T., Izawa K., Noyori R., Ikariya T. Org. Lett. 4:2002;4373-4376
25. Palmer M.J., Wills M. Tetrahedron: Asymmetry. 10:1999;2045-2061
26. Cross D.J., Kenny J.A., Houson I., Campbell L., Walsgrove T., Wills M. Tetrahedron: Asymmetry. 12:2001;1801-1806
27. Bayston D.J., Travers C.B., Polywka M.E.C. Tetrahedron: Asymmetry. 9:1998;2015-2018
28. Kenny J.A., Palmer M.J., Smith A.R.C., Walsgrove T., Wills M. Synlett. 10:1999;1615-1617
29. (e) Ma, Y., Liu, H., Chen, L., Cui, L., Zhu, J., Deng, J 2003, 5, 2103-2106.
30. (f) Blacker, A. J.; Mellor, B. J. WO 9842643, 1998.
31. Everaere K., Mortreux A., Bulliard M., Brussee J., van der Gen A., Nowogrocki G., Carpentier J.F. Eur. J. Org. Chem. 66:2001;275-291
32. Hannedouche J., Kenny J.A., Walsgrove T., Wills M. Synlett. 13:2002;263-266
33. Palmer M.J., Kenny J.A., Walsgrove T., Kawamoto A.M., Wills M. J. Chem. Soc., Perkin Trans. 1. 2002;416-427
34. Hannedouche J., Clarkson G.J., Wills M. J. Am. Chem. Soc. 126:2004;986-987
35. Cossy J., Eustache F., Dalko P.I. Tetrahedron Lett. 42:2001;5005-5007
36. Adkins H., Elofson R.M., Rossow A.G., Robinson C.C. J. Am. Chem. Soc. 71:1949;3622-3829
37. Recently, a kg-scale reaction of (R)-2-amino-1-(3-pyridinyl)ethanol was reported Duquette J., Zhang M., Zhu L., Reeves R.S. Org. Proc. Res. Dev. 7:2003;285-288
38. Watanabe M., Murata K., Ikariya T. J. Org. Chem. 67:2002;1712-1715
39. Murata K., Okano K., Miyagi M., Iwane H., Noyori R., Ikariya T. Org. Lett. 1:1999;1119-1121
40. Okano K., Murata K., Ikariya T. Tetrahedron Lett. 41:2000;9277-9280
41. Koike T., Murata K., Ikariya T. Org. Lett. 2:2000;3833-3836
42. Murata K., Konishi H., Ito M., Ikariya T. Organometallics. 21:2002;253-255
43. Watanabe M., Murata K., Ikariya T. J. Am. Chem. Soc. 125:2003;7508-7609
44. Ikariya T., Wang H., Watanabe M., Murata K. J. Organomet. Chem. 689:2004;1377-1381
45. In the case of alkanal-d1, the enantioselectivity is 24% ee; see Yamada I., Noyori R. Org. Lett. 2:2000;3425-3427
46. Commercially available from Aldrich
47. Wei Z., Li Z., Lin G. Tetrahedron. 54:1998;13059-13072
48. Spelberg J.H.L., Van Hylckama Vlieg J.E.T., Bosma T., Kellogg R.M., Janssen D.B. Tetrahedron: Asymmetry. 10:1999;2863-2870
49. Basavaiah D., Reddy G.J., Chandrashekar V. Tetrahedron: Asymmetry. 12:2001;685-689
50. Brunel J.M., Legrand O., Buono G. Eur. J. Org. Chem. 19:2000;3313-3321
51. Lautens M., Maddess M.L., Sauer E.L.O., Ouellet S.G. Org. Lett. 4:2002;83-86
52. Schubert T. Berichte des Forschungszentrums Juelich. 2002;1-175
53. Schubert T., Hummel W., Muller M. Angew. Chem., Int. Ed. Engl. 41:2002;634-637
54. Schaus S.E., Brandes B.D., Larrow J.F., Tokunaga M., Hansen K.B., Gould A.E., Furrow M.E., Jacobsen E.N. J. Am. Chem. Soc. 124:2002;1307-1315