Synthesis of Enantiomerically Pure 1,2-Diamines by Reductive Coupling of Tricarbony(benzaldimine)chromium Complexes

Synlett

Volumn 1997, Issue 1, 1997, Pages 51-53

  Taniguchi, Nobukazu ^a   Uemura, Motokazu ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002020913     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-721     Document Type: Article

References (30)

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14. Periamy, M.; Reddy, M. R.; Kanth, J. V. B. Tetrahedron Lett. 1996, 37, 4767. Pansre, S. V.; Malusare, M. G. Tetrahedron Lett. 1996, 37, 2859. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Imamoto, T.; Nishimura, S. Chem. Lett. 1990, 1141. Takai, K.; Tsubaki, Y.; Tanaka, S.; Beppu, F.; Fujiwara, Y. Chem. Lett. 1990, 203. Enholm, E. J.; Forbes, D. C.; Holub, D. P. Synth. Commun. 1990, 20, 981. Tanaka, H.; Dhimane, H.; Torii, S. Synlett 1989, 51. Mangenery, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, F. Synthesis, 1988, 255. Tanaka, H.; Dhimane, H.; Fujita, H.; Ikemoto, Y.; Torii, S. Tetrahedron Lett. 1988, 29, 3811. Betschart, C.; Schmidt, B.; Seeback, D. Helv. Chem. Acta 1988, 71, 1999. Betschart, C.; Seeback, D. Helv. Chem. Acta 1987, 70, 2215. Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152.
15. Periamy, M.; Reddy, M. R.; Kanth, J. V. B. Tetrahedron Lett. 1996, 37, 4767. Pansre, S. V.; Malusare, M. G. Tetrahedron Lett. 1996, 37, 2859. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Imamoto, T.; Nishimura, S. Chem. Lett. 1990, 1141. Takai, K.; Tsubaki, Y.; Tanaka, S.; Beppu, F.; Fujiwara, Y. Chem. Lett. 1990, 203. Enholm, E. J.; Forbes, D. C.; Holub, D. P. Synth. Commun. 1990, 20, 981. Tanaka, H.; Dhimane, H.; Torii, S. Synlett 1989, 51. Mangenery, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, F. Synthesis, 1988, 255. Tanaka, H.; Dhimane, H.; Fujita, H.; Ikemoto, Y.; Torii, S. Tetrahedron Lett. 1988, 29, 3811. Betschart, C.; Schmidt, B.; Seeback, D. Helv. Chem. Acta 1988, 71, 1999. Betschart, C.; Seeback, D. Helv. Chem. Acta 1987, 70, 2215. Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152.
16. Periamy, M.; Reddy, M. R.; Kanth, J. V. B. Tetrahedron Lett. 1996, 37, 4767. Pansre, S. V.; Malusare, M. G. Tetrahedron Lett. 1996, 37, 2859. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Imamoto, T.; Nishimura, S. Chem. Lett. 1990, 1141. Takai, K.; Tsubaki, Y.; Tanaka, S.; Beppu, F.; Fujiwara, Y. Chem. Lett. 1990, 203. Enholm, E. J.; Forbes, D. C.; Holub, D. P. Synth. Commun. 1990, 20, 981. Tanaka, H.; Dhimane, H.; Torii, S. Synlett 1989, 51. Mangenery, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, F. Synthesis, 1988, 255. Tanaka, H.; Dhimane, H.; Fujita, H.; Ikemoto, Y.; Torii, S. Tetrahedron Lett. 1988, 29, 3811. Betschart, C.; Schmidt, B.; Seeback, D. Helv. Chem. Acta 1988, 71, 1999. Betschart, C.; Seeback, D. Helv. Chem. Acta 1987, 70, 2215. Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152.
17. Periamy, M.; Reddy, M. R.; Kanth, J. V. B. Tetrahedron Lett. 1996, 37, 4767. Pansre, S. V.; Malusare, M. G. Tetrahedron Lett. 1996, 37, 2859. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Imamoto, T.; Nishimura, S. Chem. Lett. 1990, 1141. Takai, K.; Tsubaki, Y.; Tanaka, S.; Beppu, F.; Fujiwara, Y. Chem. Lett. 1990, 203. Enholm, E. J.; Forbes, D. C.; Holub, D. P. Synth. Commun. 1990, 20, 981. Tanaka, H.; Dhimane, H.; Torii, S. Synlett 1989, 51. Mangenery, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, F. Synthesis, 1988, 255. Tanaka, H.; Dhimane, H.; Fujita, H.; Ikemoto, Y.; Torii, S. Tetrahedron Lett. 1988, 29, 3811. Betschart, C.; Schmidt, B.; Seeback, D. Helv. Chem. Acta 1988, 71, 1999. Betschart, C.; Seeback, D. Helv. Chem. Acta 1987, 70, 2215. Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152.
18. Periamy, M.; Reddy, M. R.; Kanth, J. V. B. Tetrahedron Lett. 1996, 37, 4767. Pansre, S. V.; Malusare, M. G. Tetrahedron Lett. 1996, 37, 2859. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Imamoto, T.; Nishimura, S. Chem. Lett. 1990, 1141. Takai, K.; Tsubaki, Y.; Tanaka, S.; Beppu, F.; Fujiwara, Y. Chem. Lett. 1990, 203. Enholm, E. J.; Forbes, D. C.; Holub, D. P. Synth. Commun. 1990, 20, 981. Tanaka, H.; Dhimane, H.; Torii, S. Synlett 1989, 51. Mangenery, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, F. Synthesis, 1988, 255. Tanaka, H.; Dhimane, H.; Fujita, H.; Ikemoto, Y.; Torii, S. Tetrahedron Lett. 1988, 29, 3811. Betschart, C.; Schmidt, B.; Seeback, D. Helv. Chem. Acta 1988, 71, 1999. Betschart, C.; Seeback, D. Helv. Chem. Acta 1987, 70, 2215. Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152.
19. Periamy, M.; Reddy, M. R.; Kanth, J. V. B. Tetrahedron Lett. 1996, 37, 4767. Pansre, S. V.; Malusare, M. G. Tetrahedron Lett. 1996, 37, 2859. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Imamoto, T.; Nishimura, S. Chem. Lett. 1990, 1141. Takai, K.; Tsubaki, Y.; Tanaka, S.; Beppu, F.; Fujiwara, Y. Chem. Lett. 1990, 203. Enholm, E. J.; Forbes, D. C.; Holub, D. P. Synth. Commun. 1990, 20, 981. Tanaka, H.; Dhimane, H.; Torii, S. Synlett 1989, 51. Mangenery, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, F. Synthesis, 1988, 255. Tanaka, H.; Dhimane, H.; Fujita, H.; Ikemoto, Y.; Torii, S. Tetrahedron Lett. 1988, 29, 3811. Betschart, C.; Schmidt, B.; Seeback, D. Helv. Chem. Acta 1988, 71, 1999. Betschart, C.; Seeback, D. Helv. Chem. Acta 1987, 70, 2215. Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152.
20. Periamy, M.; Reddy, M. R.; Kanth, J. V. B. Tetrahedron Lett. 1996, 37, 4767. Pansre, S. V.; Malusare, M. G. Tetrahedron Lett. 1996, 37, 2859. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Imamoto, T.; Nishimura, S. Chem. Lett. 1990, 1141. Takai, K.; Tsubaki, Y.; Tanaka, S.; Beppu, F.; Fujiwara, Y. Chem. Lett. 1990, 203. Enholm, E. J.; Forbes, D. C.; Holub, D. P. Synth. Commun. 1990, 20, 981. Tanaka, H.; Dhimane, H.; Torii, S. Synlett 1989, 51. Mangenery, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, F. Synthesis, 1988, 255. Tanaka, H.; Dhimane, H.; Fujita, H.; Ikemoto, Y.; Torii, S. Tetrahedron Lett. 1988, 29, 3811. Betschart, C.; Schmidt, B.; Seeback, D. Helv. Chem. Acta 1988, 71, 1999. Betschart, C.; Seeback, D. Helv. Chem. Acta 1987, 70, 2215. Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152.
21. Periamy, M.; Reddy, M. R.; Kanth, J. V. B. Tetrahedron Lett. 1996, 37, 4767. Pansre, S. V.; Malusare, M. G. Tetrahedron Lett. 1996, 37, 2859. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Imamoto, T.; Nishimura, S. Chem. Lett. 1990, 1141. Takai, K.; Tsubaki, Y.; Tanaka, S.; Beppu, F.; Fujiwara, Y. Chem. Lett. 1990, 203. Enholm, E. J.; Forbes, D. C.; Holub, D. P. Synth. Commun. 1990, 20, 981. Tanaka, H.; Dhimane, H.; Torii, S. Synlett 1989, 51. Mangenery, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, F. Synthesis, 1988, 255. Tanaka, H.; Dhimane, H.; Fujita, H.; Ikemoto, Y.; Torii, S. Tetrahedron Lett. 1988, 29, 3811. Betschart, C.; Schmidt, B.; Seeback, D. Helv. Chem. Acta 1988, 71, 1999. Betschart, C.; Seeback, D. Helv. Chem. Acta 1987, 70, 2215. Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152.
22. Periamy, M.; Reddy, M. R.; Kanth, J. V. B. Tetrahedron Lett. 1996, 37, 4767. Pansre, S. V.; Malusare, M. G. Tetrahedron Lett. 1996, 37, 2859. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Imamoto, T.; Nishimura, S. Chem. Lett. 1990, 1141. Takai, K.; Tsubaki, Y.; Tanaka, S.; Beppu, F.; Fujiwara, Y. Chem. Lett. 1990, 203. Enholm, E. J.; Forbes, D. C.; Holub, D. P. Synth. Commun. 1990, 20, 981. Tanaka, H.; Dhimane, H.; Torii, S. Synlett 1989, 51. Mangenery, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, F. Synthesis, 1988, 255. Tanaka, H.; Dhimane, H.; Fujita, H.; Ikemoto, Y.; Torii, S. Tetrahedron Lett. 1988, 29, 3811. Betschart, C.; Schmidt, B.; Seeback, D. Helv. Chem. Acta 1988, 71, 1999. Betschart, C.; Seeback, D. Helv. Chem. Acta 1987, 70, 2215. Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152.
23. Periamy, M.; Reddy, M. R.; Kanth, J. V. B. Tetrahedron Lett. 1996, 37, 4767. Pansre, S. V.; Malusare, M. G. Tetrahedron Lett. 1996, 37, 2859. Kalyanam, N.; Rao, G. V. Tetrahedron Lett. 1993, 34, 1647. Imamoto, T.; Nishimura, S. Chem. Lett. 1990, 1141. Takai, K.; Tsubaki, Y.; Tanaka, S.; Beppu, F.; Fujiwara, Y. Chem. Lett. 1990, 203. Enholm, E. J.; Forbes, D. C.; Holub, D. P. Synth. Commun. 1990, 20, 981. Tanaka, H.; Dhimane, H.; Torii, S. Synlett 1989, 51. Mangenery, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, F. Synthesis, 1988, 255. Tanaka, H.; Dhimane, H.; Fujita, H.; Ikemoto, Y.; Torii, S. Tetrahedron Lett. 1988, 29, 3811. Betschart, C.; Schmidt, B.; Seeback, D. Helv. Chem. Acta 1988, 71, 1999. Betschart, C.; Seeback, D. Helv. Chem. Acta 1987, 70, 2215. Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152.
24. Diastereoselective coupling; Shono, T.; Kise, N.; Oike, H.; Yoshimoto, M.; Okazaki, E. Tetrahedron Lett. 1992, 33, 5559. Enantioselective pinacol coupling of imine; Shimizu, M.; Iida, T.; Fujusawa, T. Chem. Lett. 1995, 609.
25. Diastereoselective coupling; Shono, T.; Kise, N.; Oike, H.; Yoshimoto, M.; Okazaki, E. Tetrahedron Lett. 1992, 33, 5559. Enantioselective pinacol coupling of imine; Shimizu, M.; Iida, T.; Fujusawa, T. Chem. Lett. 1995, 609.
26. Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088.
27. 3): threo-adduct 5 (R = OMe); δ 1.43 (2H, s, NH), 2.48 (6H, s, NMe), 3.68 (6H, s, OMe), 3.88 (2H, s, CH), 4.87 (2H, t, J = 6.1 Hz, ArH), 4.94 (2H, d, J = 6.2 Hz, ArH), 5.52 (2H, t, J = 6.2 Hz, ArH), 5.84 (2H, d, J = 6.1 Hz, ArH). erythro-adduct 5 (R = OMe); δ 1.43 (2H, brs, NH), 2.59 (6H, s, NMe), 3.51 (6H, s, OMe), 4.19 (2H, s, CH), 4.74-4.80 (4H, m, ArH), 5.42 (2H, t, J = 6.2 Hz, ArH), 5.70 (2H, d, J = 6.1 Hz, ArH).
28. 2 solution at 0°C, and stirred for 2h and quenched with water. The mixture was extracted with ether and the extract was washed with brine, dried over MgSO4 and evaporated under reduced pressure. The residue was purified by silica gel chromatography to give 67% of the threocoupling product and 10% of the corresponding benzylamine chromium complex. The products gave satisfactory physical data
29. W = 0.041.
30. A review concerning the mechanism on acyclic selection in intermolecular rdical reactions, steric vs electronic controls: Smadja, W. Synlett, 1994, 1.