Asymmetric synthesis of anti- and syn-β-amino alcohols by reductive cross-coupling of transition metal-coordinated planar chiral arylaldehydes with aldimines

Journal of Organic Chemistry

Volumn 67, Issue 26, 2002, Pages 9227-9237

  Tanaka, Yoshie ^a   Taniguchi, Nobukazu ^a   Kimura, Takayuki ^a   Uemura, Motokazu ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CHROMIUM COMPOUNDS; REDUCTION;

MEDIATED CROSS COUPLING; PLANAR CHIRALITY;

CATALYST SELECTIVITY;

ACETOPHENONE; ALDEHYDE DERIVATIVE; AMINE; AMINOALCOHOL; BENZALDEHYDE DERIVATIVE; FERROCENE DERIVATIVE; IMINE; IODINE DERIVATIVE; LIGAND; N TOSYLFERROCENYLIDENEAMINE; SAMARIUM; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; KINETICS; SYNTHESIS;

EID: 0037184772     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0205412     Document Type: Article

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30. Some representative dl selective pinacol coupling: (a) Handa, Y.; Inanaga J. Tetrahedron Lett. 1987, 28, 5717. (b) Szymoniak, J.; Besançon, J.; Moise, C. Tetrahedron 1992, 48, 3867. (c) Suzuki, H.; Manabe, H.; Enokiya, R.; Hanazaki, Y. Chem. Lett. 1986, 1339. (d) Raubenheimer, H. G.; Seebach, D. Chimica 1986, 40, 12. (e) Clerici, A.; Clerici, L.; Porta, O. Tetrahedron Lett. 1996, 37, 3035. (f) Gansäuer, A. J. Chem. Soc., Chem. Soc. 1997, 457. Gansäuer, A. Synlett 1997, 363. (g) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293. (h) Hirao, T.; Hasegawa, T.; Muguruma, Y.; Ikeda, I. J. Org. Chem. 1996, 61, 366. (i) Nomura, R.; Matsuno, T.; Endo, T. J. Am. Chem. Soc. 1996, 118, 11666. (j) Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484 and references therein.
31. Some representative dl selective pinacol coupling: (a) Handa, Y.; Inanaga J. Tetrahedron Lett. 1987, 28, 5717. (b) Szymoniak, J.; Besançon, J.; Moise, C. Tetrahedron 1992, 48, 3867. (c) Suzuki, H.; Manabe, H.; Enokiya, R.; Hanazaki, Y. Chem. Lett. 1986, 1339. (d) Raubenheimer, H. G.; Seebach, D. Chimica 1986, 40, 12. (e) Clerici, A.; Clerici, L.; Porta, O. Tetrahedron Lett. 1996, 37, 3035. (f) Gansäuer, A. J. Chem. Soc., Chem. Soc. 1997, 457. Gansäuer, A. Synlett 1997, 363. (g) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293. (h) Hirao, T.; Hasegawa, T.; Muguruma, Y.; Ikeda, I. J. Org. Chem. 1996, 61, 366. (i) Nomura, R.; Matsuno, T.; Endo, T. J. Am. Chem. Soc. 1996, 118, 11666. (j) Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484 and references therein.
32. Some representative dl selective pinacol coupling: (a) Handa, Y.; Inanaga J. Tetrahedron Lett. 1987, 28, 5717. (b) Szymoniak, J.; Besançon, J.; Moise, C. Tetrahedron 1992, 48, 3867. (c) Suzuki, H.; Manabe, H.; Enokiya, R.; Hanazaki, Y. Chem. Lett. 1986, 1339. (d) Raubenheimer, H. G.; Seebach, D. Chimica 1986, 40, 12. (e) Clerici, A.; Clerici, L.; Porta, O. Tetrahedron Lett. 1996, 37, 3035. (f) Gansäuer, A. J. Chem. Soc., Chem. Soc. 1997, 457. Gansäuer, A. Synlett 1997, 363. (g) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293. (h) Hirao, T.; Hasegawa, T.; Muguruma, Y.; Ikeda, I. J. Org. Chem. 1996, 61, 366. (i) Nomura, R.; Matsuno, T.; Endo, T. J. Am. Chem. Soc. 1996, 118, 11666. (j) Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484 and references therein.
33. Some representative dl selective pinacol coupling: (a) Handa, Y.; Inanaga J. Tetrahedron Lett. 1987, 28, 5717. (b) Szymoniak, J.; Besançon, J.; Moise, C. Tetrahedron 1992, 48, 3867. (c) Suzuki, H.; Manabe, H.; Enokiya, R.; Hanazaki, Y. Chem. Lett. 1986, 1339. (d) Raubenheimer, H. G.; Seebach, D. Chimica 1986, 40, 12. (e) Clerici, A.; Clerici, L.; Porta, O. Tetrahedron Lett. 1996, 37, 3035. (f) Gansäuer, A. J. Chem. Soc., Chem. Soc. 1997, 457. Gansäuer, A. Synlett 1997, 363. (g) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293. (h) Hirao, T.; Hasegawa, T.; Muguruma, Y.; Ikeda, I. J. Org. Chem. 1996, 61, 366. (i) Nomura, R.; Matsuno, T.; Endo, T. J. Am. Chem. Soc. 1996, 118, 11666. (j) Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484 and references therein.
34. Some representative dl selective pinacol coupling: (a) Handa, Y.; Inanaga J. Tetrahedron Lett. 1987, 28, 5717. (b) Szymoniak, J.; Besançon, J.; Moise, C. Tetrahedron 1992, 48, 3867. (c) Suzuki, H.; Manabe, H.; Enokiya, R.; Hanazaki, Y. Chem. Lett. 1986, 1339. (d) Raubenheimer, H. G.; Seebach, D. Chimica 1986, 40, 12. (e) Clerici, A.; Clerici, L.; Porta, O. Tetrahedron Lett. 1996, 37, 3035. (f) Gansäuer, A. J. Chem. Soc., Chem. Soc. 1997, 457. Gansäuer, A. Synlett 1997, 363. (g) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293. (h) Hirao, T.; Hasegawa, T.; Muguruma, Y.; Ikeda, I. J. Org. Chem. 1996, 61, 366. (i) Nomura, R.; Matsuno, T.; Endo, T. J. Am. Chem. Soc. 1996, 118, 11666. (j) Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484 and references therein.
35. Some representative dl selective pinacol coupling: (a) Handa, Y.; Inanaga J. Tetrahedron Lett. 1987, 28, 5717. (b) Szymoniak, J.; Besançon, J.; Moise, C. Tetrahedron 1992, 48, 3867. (c) Suzuki, H.; Manabe, H.; Enokiya, R.; Hanazaki, Y. Chem. Lett. 1986, 1339. (d) Raubenheimer, H. G.; Seebach, D. Chimica 1986, 40, 12. (e) Clerici, A.; Clerici, L.; Porta, O. Tetrahedron Lett. 1996, 37, 3035. (f) Gansäuer, A. J. Chem. Soc., Chem. Soc. 1997, 457. Gansäuer, A. Synlett 1997, 363. (g) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293. (h) Hirao, T.; Hasegawa, T.; Muguruma, Y.; Ikeda, I. J. Org. Chem. 1996, 61, 366. (i) Nomura, R.; Matsuno, T.; Endo, T. J. Am. Chem. Soc. 1996, 118, 11666. (j) Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484 and references therein.
36. Some representative dl selective pinacol coupling: (a) Handa, Y.; Inanaga J. Tetrahedron Lett. 1987, 28, 5717. (b) Szymoniak, J.; Besançon, J.; Moise, C. Tetrahedron 1992, 48, 3867. (c) Suzuki, H.; Manabe, H.; Enokiya, R.; Hanazaki, Y. Chem. Lett. 1986, 1339. (d) Raubenheimer, H. G.; Seebach, D. Chimica 1986, 40, 12. (e) Clerici, A.; Clerici, L.; Porta, O. Tetrahedron Lett. 1996, 37, 3035. (f) Gansäuer, A. J. Chem. Soc., Chem. Soc. 1997, 457. Gansäuer, A. Synlett 1997, 363. (g) Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challand, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293. (h) Hirao, T.; Hasegawa, T.; Muguruma, Y.; Ikeda, I. J. Org. Chem. 1996, 61, 366. (i) Nomura, R.; Matsuno, T.; Endo, T. J. Am. Chem. Soc. 1996, 118, 11666. (j) Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484 and references therein.
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39. Formation of 1,2-diols with moderate enantioselectivity by the pinacol coupling in the presence of a chiral source. Seebach, D.; Daum, H. J. Am. Chem. Soc. 1971, 93, 2795. (a) Seebach, D.; Oei, H. A.; Daum, H. Chem. Ber. 1977, 110, 2316. (b) Matsubara, S.; Hashimoto, Y.; Okano, T.; Utimoto, K. Synlett 1999, 1411. (c) Bandini, M.; Cozzi, G.; Morganti, S.; Umani-Ronchi, A. Tetrahedron Lett. 1999, 40, 1997. (d) Taniguchi, N.; Uemura, M. Tetrahedron 1998, 54, 12775.
40. Formation of 1,2-diols with moderate enantioselectivity by the pinacol coupling in the presence of a chiral source. Seebach, D.; Daum, H. J. Am. Chem. Soc. 1971, 93, 2795. (a) Seebach, D.; Oei, H. A.; Daum, H. Chem. Ber. 1977, 110, 2316. (b) Matsubara, S.; Hashimoto, Y.; Okano, T.; Utimoto, K. Synlett 1999, 1411. (c) Bandini, M.; Cozzi, G.; Morganti, S.; Umani-Ronchi, A. Tetrahedron Lett. 1999, 40, 1997. (d) Taniguchi, N.; Uemura, M. Tetrahedron 1998, 54, 12775.
41. Formation of 1,2-diols with moderate enantioselectivity by the pinacol coupling in the presence of a chiral source. Seebach, D.; Daum, H. J. Am. Chem. Soc. 1971, 93, 2795. (a) Seebach, D.; Oei, H. A.; Daum, H. Chem. Ber. 1977, 110, 2316. (b) Matsubara, S.; Hashimoto, Y.; Okano, T.; Utimoto, K. Synlett 1999, 1411. (c) Bandini, M.; Cozzi, G.; Morganti, S.; Umani-Ronchi, A. Tetrahedron Lett. 1999, 40, 1997. (d) Taniguchi, N.; Uemura, M. Tetrahedron 1998, 54, 12775.
42. Formation of 1,2-diols with moderate enantioselectivity by the pinacol coupling in the presence of a chiral source. Seebach, D.; Daum, H. J. Am. Chem. Soc. 1971, 93, 2795. (a) Seebach, D.; Oei, H. A.; Daum, H. Chem. Ber. 1977, 110, 2316. (b) Matsubara, S.; Hashimoto, Y.; Okano, T.; Utimoto, K. Synlett 1999, 1411. (c) Bandini, M.; Cozzi, G.; Morganti, S.; Umani-Ronchi, A. Tetrahedron Lett. 1999, 40, 1997. (d) Taniguchi, N.; Uemura, M. Tetrahedron 1998, 54, 12775.
43. (a) Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088.
44. (b) Tanuguchi, N.; Uemura, M. Synlett 1997, 51.
45. (c) Taniguchi, N.; Uemura, M. Tetrahedron Lett. 1998, 39, 5385.
46. Selected recent C-C bond construction approach for β-amino alcohols. (a) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. (c) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. (d) Kobayashi, S.; Furuta, F.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. (e) Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. Org. Chem. 1996, 61, 2667. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Friestad, G. K.; Massari, S. E. Org. Lett. 2000, 2, 4237. (h) Friestad, G. K. Org. Lett. 1999, 1, 1499. (i) Tomoyasu, T.; Tomooka, K.; Nakai T. Synlett 1998, 1147.
47. Selected recent C-C bond construction approach for β-amino alcohols. (a) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. (c) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. (d) Kobayashi, S.; Furuta, F.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. (e) Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. Org. Chem. 1996, 61, 2667. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Friestad, G. K.; Massari, S. E. Org. Lett. 2000, 2, 4237. (h) Friestad, G. K. Org. Lett. 1999, 1, 1499. (i) Tomoyasu, T.; Tomooka, K.; Nakai T. Synlett 1998, 1147.
48. Selected recent C-C bond construction approach for β-amino alcohols. (a) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. (c) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. (d) Kobayashi, S.; Furuta, F.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. (e) Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. Org. Chem. 1996, 61, 2667. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Friestad, G. K.; Massari, S. E. Org. Lett. 2000, 2, 4237. (h) Friestad, G. K. Org. Lett. 1999, 1, 1499. (i) Tomoyasu, T.; Tomooka, K.; Nakai T. Synlett 1998, 1147.
49. Selected recent C-C bond construction approach for β-amino alcohols. (a) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. (c) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. (d) Kobayashi, S.; Furuta, F.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. (e) Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. Org. Chem. 1996, 61, 2667. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Friestad, G. K.; Massari, S. E. Org. Lett. 2000, 2, 4237. (h) Friestad, G. K. Org. Lett. 1999, 1, 1499. (i) Tomoyasu, T.; Tomooka, K.; Nakai T. Synlett 1998, 1147.
50. Selected recent C-C bond construction approach for β-amino alcohols. (a) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. (c) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. (d) Kobayashi, S.; Furuta, F.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. (e) Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. Org. Chem. 1996, 61, 2667. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Friestad, G. K.; Massari, S. E. Org. Lett. 2000, 2, 4237. (h) Friestad, G. K. Org. Lett. 1999, 1, 1499. (i) Tomoyasu, T.; Tomooka, K.; Nakai T. Synlett 1998, 1147.
51. Selected recent C-C bond construction approach for β-amino alcohols. (a) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. (c) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. (d) Kobayashi, S.; Furuta, F.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. (e) Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. Org. Chem. 1996, 61, 2667. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Friestad, G. K.; Massari, S. E. Org. Lett. 2000, 2, 4237. (h) Friestad, G. K. Org. Lett. 1999, 1, 1499. (i) Tomoyasu, T.; Tomooka, K.; Nakai T. Synlett 1998, 1147.
52. Selected recent C-C bond construction approach for β-amino alcohols. (a) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. (c) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. (d) Kobayashi, S.; Furuta, F.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. (e) Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. Org. Chem. 1996, 61, 2667. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Friestad, G. K.; Massari, S. E. Org. Lett. 2000, 2, 4237. (h) Friestad, G. K. Org. Lett. 1999, 1, 1499. (i) Tomoyasu, T.; Tomooka, K.; Nakai T. Synlett 1998, 1147.
53. Selected recent C-C bond construction approach for β-amino alcohols. (a) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. (c) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. (d) Kobayashi, S.; Furuta, F.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. (e) Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. Org. Chem. 1996, 61, 2667. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Friestad, G. K.; Massari, S. E. Org. Lett. 2000, 2, 4237. (h) Friestad, G. K. Org. Lett. 1999, 1, 1499. (i) Tomoyasu, T.; Tomooka, K.; Nakai T. Synlett 1998, 1147.
54. Selected recent C-C bond construction approach for β-amino alcohols. (a) Matsuda, F.; Kawatsura, M.; Dekura, F.; Shirahama, H. J. Chem. Soc., Perkin Trans. 1 1999, 2371. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798. (c) Trost, B. M.; Lee, C. B. J. Am. Chem. Soc. 1998, 120, 6818. (d) Kobayashi, S.; Furuta, F.; Hayashi, T.; Nishijima, M.; Hanada, K. J. Am. Chem. Soc. 1998, 120, 908. (e) Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P.; Williams, D. J. Org. Chem. 1996, 61, 2667. (f) Enders, D.; Reinhold, U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (g) Friestad, G. K.; Massari, S. E. Org. Lett. 2000, 2, 4237. (h) Friestad, G. K. Org. Lett. 1999, 1, 1499. (i) Tomoyasu, T.; Tomooka, K.; Nakai T. Synlett 1998, 1147.
55. (a) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
56. (b) Denmark, S. E.; Nicaise, O. J.C. J. Chem. Soc., Chem. Commun. 1996, 999.
57. (c) Denmark, S. E.; Stiff, C. M. J. Org. Chem. 2000, 65, 5875.
58. (d) Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 268.
59. (e) Kobayashi, S.; Sugita, K.; Oyamada, H. Synlett 1999, 138.
60. (f) Davies, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
61. (g) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531.
62. (h) Reetz, M. T.; Schmitz, A. Tetrahedron Lett. 1999, 40, 2737.
63. (i) Shimizu, M.; Tsukamoto, K.; Fujisawa, T. Tetrahedron Lett. 1997, 38, 5193.
64. (j) Hoffman, R. V.; Maslouh, N.; Cervantes-Lee, F. J. Org. Chem. 2002, 67, 1045.
65. List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827.
66. An intermolecular cross-coupling between carbonyls and imines for synthesis of β-amino alcohols: (a) Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 6551. (b) Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. (c) Shono, T.; Kise, N.; Kunimi, N.; Nomura, R. Chem. Lett. 1991, 2191. (d) Shono, T.; Kise, N.; Fujimoto, T.; Yamanami, A.; Nomura, R. J. Org. Chem. 1994, 59, 1730. (e) Machrouhi, H.; Namy, J.-L. Tetrahedron Lett. 1999, 40, 1315. (f) Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. (g) Guijarro, D.; Yus, M. Tetrahedron 1993, 49, 7761.
67. An intermolecular cross-coupling between carbonyls and imines for synthesis of β-amino alcohols: (a) Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 6551. (b) Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. (c) Shono, T.; Kise, N.; Kunimi, N.; Nomura, R. Chem. Lett. 1991, 2191. (d) Shono, T.; Kise, N.; Fujimoto, T.; Yamanami, A.; Nomura, R. J. Org. Chem. 1994, 59, 1730. (e) Machrouhi, H.; Namy, J.-L. Tetrahedron Lett. 1999, 40, 1315. (f) Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. (g) Guijarro, D.; Yus, M. Tetrahedron 1993, 49, 7761.
68. An intermolecular cross-coupling between carbonyls and imines for synthesis of β-amino alcohols: (a) Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 6551. (b) Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. (c) Shono, T.; Kise, N.; Kunimi, N.; Nomura, R. Chem. Lett. 1991, 2191. (d) Shono, T.; Kise, N.; Fujimoto, T.; Yamanami, A.; Nomura, R. J. Org. Chem. 1994, 59, 1730. (e) Machrouhi, H.; Namy, J.-L. Tetrahedron Lett. 1999, 40, 1315. (f) Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. (g) Guijarro, D.; Yus, M. Tetrahedron 1993, 49, 7761.
69. An intermolecular cross-coupling between carbonyls and imines for synthesis of β-amino alcohols: (a) Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 6551. (b) Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. (c) Shono, T.; Kise, N.; Kunimi, N.; Nomura, R. Chem. Lett. 1991, 2191. (d) Shono, T.; Kise, N.; Fujimoto, T.; Yamanami, A.; Nomura, R. J. Org. Chem. 1994, 59, 1730. (e) Machrouhi, H.; Namy, J.-L. Tetrahedron Lett. 1999, 40, 1315. (f) Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. (g) Guijarro, D.; Yus, M. Tetrahedron 1993, 49, 7761.
70. An intermolecular cross-coupling between carbonyls and imines for synthesis of β-amino alcohols: (a) Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 6551. (b) Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. (c) Shono, T.; Kise, N.; Kunimi, N.; Nomura, R. Chem. Lett. 1991, 2191. (d) Shono, T.; Kise, N.; Fujimoto, T.; Yamanami, A.; Nomura, R. J. Org. Chem. 1994, 59, 1730. (e) Machrouhi, H.; Namy, J.-L. Tetrahedron Lett. 1999, 40, 1315. (f) Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. (g) Guijarro, D.; Yus, M. Tetrahedron 1993, 49, 7761.
71. An intermolecular cross-coupling between carbonyls and imines for synthesis of β-amino alcohols: (a) Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 6551. (b) Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. (c) Shono, T.; Kise, N.; Kunimi, N.; Nomura, R. Chem. Lett. 1991, 2191. (d) Shono, T.; Kise, N.; Fujimoto, T.; Yamanami, A.; Nomura, R. J. Org. Chem. 1994, 59, 1730. (e) Machrouhi, H.; Namy, J.-L. Tetrahedron Lett. 1999, 40, 1315. (f) Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. (g) Guijarro, D.; Yus, M. Tetrahedron 1993, 49, 7761.
72. An intermolecular cross-coupling between carbonyls and imines for synthesis of β-amino alcohols: (a) Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 6551. (b) Shono, T.; Kise, N.; Fujimoto, T. Tetrahedron Lett. 1991, 32, 525. (c) Shono, T.; Kise, N.; Kunimi, N.; Nomura, R. Chem. Lett. 1991, 2191. (d) Shono, T.; Kise, N.; Fujimoto, T.; Yamanami, A.; Nomura, R. J. Org. Chem. 1994, 59, 1730. (e) Machrouhi, H.; Namy, J.-L. Tetrahedron Lett. 1999, 40, 1315. (f) Hanamoto, T.; Inanaga, J. Tetrahedron Lett. 1991, 32, 3555. (g) Guijarro, D.; Yus, M. Tetrahedron 1993, 49, 7761.
73. Preliminary report; Taniguchi, N.; Uemura, M. J. Am. Chem. Soc. 2000, 122, 8301.
74. Riant, O.; Samuel, O.; Flessner, T.; Taudien, S.; Kagan, H. B. J. Org. Chem. 1997, 62, 6733.
75. w = 0.044.
76. 4NF, (vi) aq HCl.
77. w = 0.190.
78. Optically pure o-methoxy and methylbenzaldehyde chromium complexes were obtained by separation of diastereomers derived from L-valinol with column chromatography according to the literature method: (a) Davies, S. G.; Goodfellow, C. L. J. Chem. Soc., Perkin Trans. 1 1989, 192. (b) Davies, S. G.; Goodfellow, C. L. J. Chem. Soc., Perkin Trans. 1 1990, 393. (c) Bromley, L. A.; Davies, S. G.; Goodfellow, C. L. Tetrahedron: Asymmetry 1991, 2, 139.
79. Optically pure o-methoxy and methylbenzaldehyde chromium complexes were obtained by separation of diastereomers derived from L-valinol with column chromatography according to the literature method: (a) Davies, S. G.; Goodfellow, C. L. J. Chem. Soc., Perkin Trans. 1 1989, 192. (b) Davies, S. G.; Goodfellow, C. L. J. Chem. Soc., Perkin Trans. 1 1990, 393. (c) Bromley, L. A.; Davies, S. G.; Goodfellow, C. L. Tetrahedron: Asymmetry 1991, 2, 139.
80. Optically pure o-methoxy and methylbenzaldehyde chromium complexes were obtained by separation of diastereomers derived from L-valinol with column chromatography according to the literature method: (a) Davies, S. G.; Goodfellow, C. L. J. Chem. Soc., Perkin Trans. 1 1989, 192. (b) Davies, S. G.; Goodfellow, C. L. J. Chem. Soc., Perkin Trans. 1 1990, 393. (c) Bromley, L. A.; Davies, S. G.; Goodfellow, C. L. Tetrahedron: Asymmetry 1991, 2, 139.
81. w = 0.077.
82. Predominant anti conformation of the C=O or C=N double bond to the ortho substituents of ferrocenyl compounds was proposed by diastereoselective nucleophilic addition to the double bond. For a review see: Ferrocenes; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995.
83. α-Ferrocenyl lithium derivatives have similar stereochemical character for the electrophilic quenching depending on the α-position in the presence or absence of an ortho substituent on the Cp ring. Ireland, T.; Perea, J. J. A.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 1457.
84. A mechanism of acyclic selection in intermolecular radical reactions and intramolecular radical cyclization. (a) Smadja, W. Synlett 1994, 1. (b) Bobo, S.; Storch de Gracia, I.; Chiara, J. S. Synlett 1999, 1551. (c) Boiron, A.; Zillig, P.; Faber, D.; Giese, B. J. Org. Chem. 1998, 63, 5877.
85. A mechanism of acyclic selection in intermolecular radical reactions and intramolecular radical cyclization. (a) Smadja, W. Synlett 1994, 1. (b) Bobo, S.; Storch de Gracia, I.; Chiara, J. S. Synlett 1999, 1551. (c) Boiron, A.; Zillig, P.; Faber, D.; Giese, B. J. Org. Chem. 1998, 63, 5877.
86. A mechanism of acyclic selection in intermolecular radical reactions and intramolecular radical cyclization. (a) Smadja, W. Synlett 1994, 1. (b) Bobo, S.; Storch de Gracia, I.; Chiara, J. S. Synlett 1999, 1551. (c) Boiron, A.; Zillig, P.; Faber, D.; Giese, B. J. Org. Chem. 1998, 63, 5877.
87. A preliminary report: Tanaka, Y.; Taniguchi, N.; Uemura, M. Org. Lett. 2002, 4, 835.
88. The coordination of a tricarbonylchromium fragment to the arene ring was found to also increase the diastereoselectivity in the asymmetric allyboration of aromatic aldehydes: Roush, W. R.; Park, J. C. J. Org. Chem. 1990, 55, 1143.
89. Authentic N-tosyl-2-amino-1,2-diphenylethyl alcohol derivative was prepared by the following literature procedure: (a) Davis, F. A.; Hague, M. S.; Przeslawski, R. M. J. Org. Chem. 1989, 54, 2021. (b) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141. The corresponding syn-β-amino alcohol: (c) Reetz, M. T.; Drewes, M. W.; Lennick, K.; Schmitz, A.; Holdgrün, X. Tetrahedron: Asymmetry 1990, 1, 375.
90. Authentic N-tosyl-2-amino-1,2-diphenylethyl alcohol derivative was prepared by the following literature procedure: (a) Davis, F. A.; Hague, M. S.; Przeslawski, R. M. J. Org. Chem. 1989, 54, 2021. (b) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141. The corresponding syn-β-amino alcohol: (c) Reetz, M. T.; Drewes, M. W.; Lennick, K.; Schmitz, A.; Holdgrün, X. Tetrahedron: Asymmetry 1990, 1, 375.
91. Authentic N-tosyl-2-amino-1,2-diphenylethyl alcohol derivative was prepared by the following literature procedure: (a) Davis, F. A.; Hague, M. S.; Przeslawski, R. M. J. Org. Chem. 1989, 54, 2021. (b) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141. The corresponding syn-β-amino alcohol: (c) Reetz, M. T.; Drewes, M. W.; Lennick, K.; Schmitz, A.; Holdgrün, X. Tetrahedron: Asymmetry 1990, 1, 375.
92. The absolute configuration of the syn-coupling product 34 was determined as the (R,R)-configuration by comparison of the optical rotation sign of authentic syn-β-amino alcohol derived from -2-phenylglycine according to ref 26c.
93. (a) Solladié-Cavallo, A. Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: Greenwich, CT, 1989; Vol. 1, p 99.
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96. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
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98. (d) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1992, 3, 1475.
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