Selective hydrogenation of benzophenones to benzhydrols. Asymmetric synthesis of unsymmetrical diarylmethanols

Organic Letters

Volumn 2, Issue 5, 2000, Pages 659-661

  Ohkuma, Takeshi ^a,b   Koizumi, Masatoshi ^a   Ikehira, Hideyuki ^b   Yokozawa, Tohru ^b   Noyori, Ryoji ^a,b  

^a NAGOYA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001286347     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9904139     Document Type: Article

References (54)

1. Examples include: antihistaminic and -serotonic homochlorcyclizine (Pendse, V. K.; Madan, B. R. Indian J. Physiol. Pharmacol. 1969, 13, 29-36), antihistaminic oxatomide (Awouters, F.; Niemegeers, C. J. E.; Van den Berk, J.; Van Nueten, J. M.; Lenaerts, F. M.; Borgers, M.; Schellekens, K. H. L.; Broeckaert, A.; De Cree, J.; Janssen, P. A. J. Experientia 1977, 33, 1657-1659), antihypertensive manidipine (Meguro, K.; Aizawa, M.; Sohda, T.; Kawamatsu, Y.; Nagaoka, A. Chem. Pharm. Bull. 1985, 33, 3787-3797), antimycotic bifonazole (Regel, E.; Draber, W.; Büchel, K. H.; Plempel, M. Ger. Patent 2 461 406, 1976), and flunarizine, a calcium antagonist (Janssen, P. A. J. Fr. Patent 2 014 487, 1970).
2. Examples include: antihistaminic and -serotonic homochlorcyclizine (Pendse, V. K.; Madan, B. R. Indian J. Physiol. Pharmacol. 1969, 13, 29-36), antihistaminic oxatomide (Awouters, F.; Niemegeers, C. J. E.; Van den Berk, J.; Van Nueten, J. M.; Lenaerts, F. M.; Borgers, M.; Schellekens, K. H. L.; Broeckaert, A.; De Cree, J.; Janssen, P. A. J. Experientia 1977, 33, 1657-1659), antihypertensive manidipine (Meguro, K.; Aizawa, M.; Sohda, T.; Kawamatsu, Y.; Nagaoka, A. Chem. Pharm. Bull. 1985, 33, 3787-3797), antimycotic bifonazole (Regel, E.; Draber, W.; Büchel, K. H.; Plempel, M. Ger. Patent 2 461 406, 1976), and flunarizine, a calcium antagonist (Janssen, P. A. J. Fr. Patent 2 014 487, 1970).
3. Examples include: antihistaminic and -serotonic homochlorcyclizine (Pendse, V. K.; Madan, B. R. Indian J. Physiol. Pharmacol. 1969, 13, 29-36), antihistaminic oxatomide (Awouters, F.; Niemegeers, C. J. E.; Van den Berk, J.; Van Nueten, J. M.; Lenaerts, F. M.; Borgers, M.; Schellekens, K. H. L.; Broeckaert, A.; De Cree, J.; Janssen, P. A. J. Experientia 1977, 33, 1657-1659), antihypertensive manidipine (Meguro, K.; Aizawa, M.; Sohda, T.; Kawamatsu, Y.; Nagaoka, A. Chem. Pharm. Bull. 1985, 33, 3787-3797), antimycotic bifonazole (Regel, E.; Draber, W.; Büchel, K. H.; Plempel, M. Ger. Patent 2 461 406, 1976), and flunarizine, a calcium antagonist (Janssen, P. A. J. Fr. Patent 2 014 487, 1970).
4. Examples include: antihistaminic and -serotonic homochlorcyclizine (Pendse, V. K.; Madan, B. R. Indian J. Physiol. Pharmacol. 1969, 13, 29-36), antihistaminic oxatomide (Awouters, F.; Niemegeers, C. J. E.; Van den Berk, J.; Van Nueten, J. M.; Lenaerts, F. M.; Borgers, M.; Schellekens, K. H. L.; Broeckaert, A.; De Cree, J.; Janssen, P. A. J. Experientia 1977, 33, 1657-1659), antihypertensive manidipine (Meguro, K.; Aizawa, M.; Sohda, T.; Kawamatsu, Y.; Nagaoka, A. Chem. Pharm. Bull. 1985, 33, 3787-3797), antimycotic bifonazole (Regel, E.; Draber, W.; Büchel, K. H.; Plempel, M. Ger. Patent 2 461 406, 1976), and flunarizine, a calcium antagonist (Janssen, P. A. J. Fr. Patent 2 014 487, 1970).
5. Examples include: antihistaminic and -serotonic homochlorcyclizine (Pendse, V. K.; Madan, B. R. Indian J. Physiol. Pharmacol. 1969, 13, 29-36), antihistaminic oxatomide (Awouters, F.; Niemegeers, C. J. E.; Van den Berk, J.; Van Nueten, J. M.; Lenaerts, F. M.; Borgers, M.; Schellekens, K. H. L.; Broeckaert, A.; De Cree, J.; Janssen, P. A. J. Experientia 1977, 33, 1657-1659), antihypertensive manidipine (Meguro, K.; Aizawa, M.; Sohda, T.; Kawamatsu, Y.; Nagaoka, A. Chem. Pharm. Bull. 1985, 33, 3787-3797), antimycotic bifonazole (Regel, E.; Draber, W.; Büchel, K. H.; Plempel, M. Ger. Patent 2 461 406, 1976), and flunarizine, a calcium antagonist (Janssen, P. A. J. Fr. Patent 2 014 487, 1970).
6. 3COOH afforded diphenylmethane exclusively.
7. Sajiki, H.; Hattori, K.; Hirota, K. J. Chem. Soc., Perkin Trans. 1 1998, 4043-4044.
8. (a) Werbel, L. M.; Elslager, E. F.; Pearlman, W. M. J. Org. Chem. 1964, 29, 967-968.
9. (b) Gosser, L. W. U.S. Patent 4 302 435, 1981.
10. (c) Kumbhar, P. S.; Rajadhyaksha, R. A. Stud. Surf. Sci. Catal. 1993, 78, 251-258.
11. (a) Blum, Y.; Czarkie, D.; Rahamim, Y.; Shvo, Y. Organometallics 1985, 4, 1459-1461.
12. (b) Linn, D. E., Jr.; Halpern, J. J. Organomet. Chem. 1987, 330, 155-159.
13. (c) Lau, C.-P.; Cheng, L. J. Mol. Catal. 1993, 84, 39-50.
14. Walling, C.; Bollyky, L. J. Am. Chem. Soc. 1964, 86, 3750-3752.
15. Transfer hydrogenation: (a) Kleinfelter, D. C. J. Org. Chem. 1967, 32, 840-842.
16. (b) Mestroni, G.; Zassinovich, G.; Camus, A.; Martinelli, F. J. Organomet. Chem. 1980, 198, 87-96.
17. (c) Ram, S.; Spicer, L. D. Synth. Commun. 1992, 22, 2673-2681.
18. (d) Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521-2522.
19. (e) Mizushima, E.; Yamaguchi, M.; Yamagishi, T. Chem. Lett. 1997, 237-238.
20. Another standard method benzhydrol preparetion is via the addition of arylmetals to benzaldehydes.
21. (a) Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703-1707.
22. (b) Ohkuma, T.; Koizumi, M.; Doucet, H.; Pham, T.; Kozawa, M.; Murata, K.; Katayama, E.; Yokozawa, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 13529-13530.
23. See also: (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676.
24. (b) Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417-10418.
25. (c) Ohkuma, T.; Ooka, H.; Yamakawa, M.; Ikariya, T.; Noyori, R. J. Org. Chem. 1996, 61, 4872-4873.
26. (d) Ohkuma, T.; Ikehira, H.; Ikariya, T.; Noyori, R. Synlett 1997, 467-468.
27. (e) Ohkuma, T.; Doucet, H.; Pham, T.; Mikami, K.; Korenaga, T.; Terada, M.; Noyori, R. J. Am. Chem. Soc. 1998, 120, 1086-1087.
28. (f) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497.
29. Hammett, L. P. Physical Organic Chemistry, 2nd ed.; McGraw-Hill: New York, 1970; Chapter 11.
30. 4 reduction of ketones, see: Brown, H. C.; Wheeler, O. H.; Ichikawa, K. Tetrahedron 1957, 1, 214-220.
31. (a) Bowden, K.; Hardy, M. Tetrahedron 1966, 22, 1169-1174.
32. (b) Bruce, G. T.; Cooksey, A. R.; Morgan, K. J. J. Chem. Soc., Perkin Trans. 2 1975, 551-553.
33. XylBINAP = 2.2′-bis(di-3,5-xylylphosphino)-1,1′-binaphthyl. Tol-BINAP = 2,2′-bis(di-4-tolylyphosphino)-1,1′-binaphthyl. DAIPEN = 1,1-di(4-anisyl)-2-isopropyl-1.2-ethylenediamine.
34. For asymmetric reduction of diaryl ketones using silicon-and boron-based hydrides, see: (a) Peyronel, J.-F.; Fiaud, J.-C.; Kagan, H. B. J. Chem. Res. Miniprint 1980, 4057-4080.
35. (b) Brunner, H.; Kürzinger, A. J. Organomet. Chem. 1988, 346, 413-424.
36. (c) Brown, E.; Penfornis, A.; Bayma, J.; Touet J. Tetrahedron: Asymmetry 1991, 2, 339-342.
37. (d) Brown E, Lézé A, Touet J. Tetrahedron: Asymmetry 1992, 3, 841-844.
38. (e) Shieh, W.-C.; Cantrell, W. R., Jr.; Carlson, J. A. Tetrahedron Lett. 1995, 36, 3797-3800.
39. (f) Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205-2208.
40. (g) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012. and references therein.
41. 2 to benzaldehydes, see: (a) Weber, B.; Seebach, D. Tetrahedron 1994, 50, 7473-7484.
42. (b) Dosa, P. I.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1997, 62, 444-445.
43. (c) Bolm, C.; Muñiz, K. Chem. Commun. 1999, 1295-1296.
44. (d) Huang, W.-S.; Pu, L. J. Org. Chem. 1999, 64, 4222-4223.
45. (a) Watanabe, M.; Kuwahara, S.; Harada, N.; Koizumi, M.; Ohkuma, T. Tetrahedron: Asymmetry 1999, 10, 2075-2078.
46. (b) Kuwahara, S.; Watanabe, M.; Harada, N.; Koizumi, M.; Ohkuma, T. Enantiomer, in press. See also: Harada, N.; Fujita, K.; Watanabe, M. Enantiomer 1997, 2, 359-366. Harada, N.; Fujita, K.; Watanabe, M. Enantiomer 1998, 3, 64-70.
47. (b) Kuwahara, S.; Watanabe, M.; Harada, N.; Koizumi, M.; Ohkuma, T. Enantiomer, in press. See also: Harada, N.; Fujita, K.; Watanabe, M. Enantiomer 1997, 2, 359-366. Harada, N.; Fujita, K.; Watanabe, M. Enantiomer 1998, 3, 64-70.
48. (b) Kuwahara, S.; Watanabe, M.; Harada, N.; Koizumi, M.; Ohkuma, T. Enantiomer, in press. See also: Harada, N.; Fujita, K.; Watanabe, M. Enantiomer 1997, 2, 359-366. Harada, N.; Fujita, K.; Watanabe, M. Enantiomer 1998, 3, 64-70.
49. 17
50. (a) van der Stelt, C.; Heus, W. J.; Nauta, W. T. Arzneim.-Forsch. 1969, 19, 2010-2012.
51. (b) Rekker, R. F.; Timmerman, H.; Harms, A. F.; Nauta, W. T. Arzneim.-Forsch. 1971, 21, 688-691.
52. Ireland, T.; Perea, J. J. A.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 1457-1460.
53. Zuccarello, F.; Millefiori, S.; Trovato, S. Can. J. Chem. 1976, 54, 226-230.
54. Casy, A. F.; Drake, A. F.; Ganellin, C. R.; Mercer, A. D.; Upton, C. Chirality 1992, 4, 356-366.