Enantioselective borohydride reduction of N-diphenylphosphinyl imines using optically active cobalt(II) complex catalysts

Chemistry Letters

Volumn , Issue 6, 1997, Pages 493-494

  Sugi, Kiyoaki D ^a   Nagata, Takushi ^a   Yamada, Tohru ^a   Mukaiyama, Teruaki ^b  

^a MITSUI CHEMICALS INC   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031518728     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.493     Document Type: Article

References (35)

1. Reviews: R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wily & Sons, New York (1994), Chap. 2; A. Togni and L. M. Venanzi, Angew. Chem., Int. Ed. Engl., 33, 497 (1994); A. H. Hoveyda and J. P. Morken, Angew. Chem., Int. Ed. Engl., 35, 1263 (1996).
2. Reviews: R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wily & Sons, New York (1994), Chap. 2; A. Togni and L. M. Venanzi, Angew. Chem., Int. Ed. Engl., 33, 497 (1994); A. H. Hoveyda and J. P. Morken, Angew. Chem., Int. Ed. Engl., 35, 1263 (1996).
3. Reviews: R. Noyori, "Asymmetric Catalysis in Organic Synthesis," John Wily & Sons, New York (1994), Chap. 2; A. Togni and L. M. Venanzi, Angew. Chem., Int. Ed. Engl., 33, 497 (1994); A. H. Hoveyda and J. P. Morken, Angew. Chem., Int. Ed. Engl., 35, 1263 (1996).
4. Reviews: Q.-C. Zhu and R. O. Hutchins, Org. Prep. Proced. Int., 26, 193 (1994); B. R. James, Chem. Ind. (Dekker),62, 167 (1995); A. Johansson, Contemporary Org. Syn., 1996, 393.
5. Reviews: Q.-C. Zhu and R. O. Hutchins, Org. Prep. Proced. Int., 26, 193 (1994); B. R. James, Chem. Ind. (Dekker),62, 167 (1995); A. Johansson, Contemporary Org. Syn., 1996, 393.
6. Reviews: Q.-C. Zhu and R. O. Hutchins, Org. Prep. Proced. Int., 26, 193 (1994); B. R. James, Chem. Ind. (Dekker),62, 167 (1995); A. Johansson, Contemporary Org. Syn., 1996, 393.
7. M. J. Burk, J. P. Martinez, J. E. Feaster, and N. Cosford, Tetrahedron, 50, 4399 (1994); K. Tani, J. Onouchi, T. Yamagata, and Y. Kataoka, Chem. Lett., 1995, 955; T. Morimoto and K. Achiwa, Tetrahedron: Asymmetry, 6, 2661 (1995), and references were cited therein.
8. M. J. Burk, J. P. Martinez, J. E. Feaster, and N. Cosford, Tetrahedron, 50, 4399 (1994); K. Tani, J. Onouchi, T. Yamagata, and Y. Kataoka, Chem. Lett., 1995, 955; T. Morimoto and K. Achiwa, Tetrahedron: Asymmetry, 6, 2661 (1995), and references were cited therein.
9. M. J. Burk, J. P. Martinez, J. E. Feaster, and N. Cosford, Tetrahedron, 50, 4399 (1994); K. Tani, J. Onouchi, T. Yamagata, and Y. Kataoka, Chem. Lett., 1995, 955; T. Morimoto and K. Achiwa, Tetrahedron: Asymmetry, 6, 2661 (1995), and references were cited therein.
10. N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya, and R. Noyori, J. Am. Chem. Soc., 118, 4916 (1996), and references were cited therein.
11. X. Verdaguer, U. E. W. Lange, M. T. Reding, and S. L. Buchwald, J. Am. Chem. Soc., 118, 6784 (1996), and references were cited therein.
12. M. Shimizu, M. Kamei, and T. Fujisawa, Tetrahedron Lett., 36, 8607 (1995), and references were cited therein.
13. (S, S) and (R, R) cobalt(II) complex A are available from Tokyo Kasei Kogyo Co., Ltd.
14. T. Nagata, K. Yorozu, T. Yamada, and T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 34, 2145 (1995); K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem Lett., 1996, 737; T. Nagata, K. D. Sugi, T. Yamada, and T. Mukaiyama, Synlett, 1996, 1076; K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem Lett., 1996, 1081.
15. T. Nagata, K. Yorozu, T. Yamada, and T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 34, 2145 (1995); K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem Lett., 1996, 737; T. Nagata, K. D. Sugi, T. Yamada, and T. Mukaiyama, Synlett, 1996, 1076; K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem Lett., 1996, 1081.
16. T. Nagata, K. Yorozu, T. Yamada, and T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 34, 2145 (1995); K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem Lett., 1996, 737; T. Nagata, K. D. Sugi, T. Yamada, and T. Mukaiyama, Synlett, 1996, 1076; K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem Lett., 1996, 1081.
17. T. Nagata, K. Yorozu, T. Yamada, and T. Mukaiyama, Angew. Chem., Int. Ed. Engl., 34, 2145 (1995); K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem Lett., 1996, 737; T. Nagata, K. D. Sugi, T. Yamada, and T. Mukaiyama, Synlett, 1996, 1076; K. D. Sugi, T. Nagata, T. Yamada, and T. Mukaiyama, Chem Lett., 1996, 1081.
18. Stoichiometric and catalytic asymmetric reductions by hydride reagents; Oxime ether: S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, and S. Nakahama, Bull. Chem. Soc. Jpn., 60, 395 (1987); N-Sulfonyl imine: A. B. Charette and A. Giroux, Tetrahedron Lett., 37, 6669 (1996); N-Phosphinyl imine: R. O. Hutchins, A. Abdel-Magid, Y. P. Stercho, and A. Wambsgans, J. Org. Chem., 52, 702 (1987); Other imines: C. Bolm and M. Felder, Synlett, 1994, 655.
19. Stoichiometric and catalytic asymmetric reductions by hydride reagents; Oxime ether: S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, and S. Nakahama, Bull. Chem. Soc. Jpn., 60, 395 (1987); N-Sulfonyl imine: A. B. Charette and A. Giroux, Tetrahedron Lett., 37, 6669 (1996); N-Phosphinyl imine: R. O. Hutchins, A. Abdel-Magid, Y. P. Stercho, and A. Wambsgans, J. Org. Chem., 52, 702 (1987); Other imines: C. Bolm and M. Felder, Synlett, 1994, 655.
20. Stoichiometric and catalytic asymmetric reductions by hydride reagents; Oxime ether: S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, and S. Nakahama, Bull. Chem. Soc. Jpn., 60, 395 (1987); N-Sulfonyl imine: A. B. Charette and A. Giroux, Tetrahedron Lett., 37, 6669 (1996); N-Phosphinyl imine: R. O. Hutchins, A. Abdel-Magid, Y. P. Stercho, and A. Wambsgans, J. Org. Chem., 52, 702 (1987); Other imines: C. Bolm and M. Felder, Synlett, 1994, 655.
21. Stoichiometric and catalytic asymmetric reductions by hydride reagents; Oxime ether: S. Itsuno, Y. Sakurai, K. Ito, A. Hirao, and S. Nakahama, Bull. Chem. Soc. Jpn., 60, 395 (1987); N-Sulfonyl imine: A. B. Charette and A. Giroux, Tetrahedron Lett., 37, 6669 (1996); N-Phosphinyl imine: R. O. Hutchins, A. Abdel-Magid, Y. P. Stercho, and A. Wambsgans, J. Org. Chem., 52, 702 (1987); Other imines: C. Bolm and M. Felder, Synlett, 1994, 655.
22. 1H NMR chemical shifts of Oxime and Oxime methyl ethers: G. J. Karabatsos and N. Hsi, Tetrahedron, 23, 1079 (1967);
23. K. Maruoka, T. Miyazaki, M. Ando, Y. Matsumura, S. Sakane, K. Hattori, and H. Yamamoto, J. Am. Chem. Soc., 105, 2831 (1983); Homolytic rearrangements of O-sulfinyl or O-phosphinyl derivatives to N-sulfonyl and N-phosphinyl imines: C. Brown, R. F. Hudson, and K. A. F. Record, J. C. S. Perkin II, 1978, 822; D. L. Boger and W. L. Corbett, J. Org. Chem., 57, 4777 (1992).
24. K. Maruoka, T. Miyazaki, M. Ando, Y. Matsumura, S. Sakane, K. Hattori, and H. Yamamoto, J. Am. Chem. Soc., 105, 2831 (1983); Homolytic rearrangements of O-sulfinyl or O-phosphinyl derivatives to N-sulfonyl and N-phosphinyl imines: C. Brown, R. F. Hudson, and K. A. F. Record, J. C. S. Perkin II, 1978, 822; D. L. Boger and W. L. Corbett, J. Org. Chem., 57, 4777 (1992).
25. K. Maruoka, T. Miyazaki, M. Ando, Y. Matsumura, S. Sakane, K. Hattori, and H. Yamamoto, J. Am. Chem. Soc., 105, 2831 (1983); Homolytic rearrangements of O-sulfinyl or O-phosphinyl derivatives to N-sulfonyl and N-phosphinyl imines: C. Brown, R. F. Hudson, and K. A. F. Record, J. C. S. Perkin II, 1978, 822; D. L. Boger and W. L. Corbett, J. Org. Chem., 57, 4777 (1992).
26. 4: R. O. Hutchins, J. Adams, and M. C. Rutledge, J. Org. Chem., 60, 7396 (1995); F. A. Davis, P. Zhou, and B.-C. Chen, Phosphorus, Sulfur, and Silicon, 115, 85 (1996).
27. 4: R. O. Hutchins, J. Adams, and M. C. Rutledge, J. Org. Chem., 60, 7396 (1995); F. A. Davis, P. Zhou, and B.-C. Chen, Phosphorus, Sulfur, and Silicon, 115, 85 (1996).
28. The various imines were prepared in accord with the following method; B. Krzyzanowska and W. J. Stec, Synthesis, 1982, 270.
29. B. Krzyzanowska and W. J. Stec, Synthesis, 1978, 521; T. W. Greene and G. M. Wuts, "Protective Groups in Organic Synthesis," 2nd ed; John Wiley & Sons, New York (1991), p375; V. K. Aggarwal, A. Thompson, R. V. H. Jones, and M. C. H. Standen, J. Org Chem., 61, 8368 (1996).
30. B. Krzyzanowska and W. J. Stec, Synthesis, 1978, 521; T. W. Greene and G. M. Wuts, "Protective Groups in Organic Synthesis," 2nd ed; John Wiley & Sons, New York (1991), p375; V. K. Aggarwal, A. Thompson, R. V. H. Jones, and M. C. H. Standen, J. Org Chem., 61, 8368 (1996).
31. B. Krzyzanowska and W. J. Stec, Synthesis, 1978, 521; T. W. Greene and G. M. Wuts, "Protective Groups in Organic Synthesis," 2nd ed; John Wiley & Sons, New York (1991), p375; V. K. Aggarwal, A. Thompson, R. V. H. Jones, and M. C. H. Standen, J. Org Chem., 61, 8368 (1996).
32. Free amines were assigned as (S) configuration by comparison of sign of optical rotation with literature value, and thusN-phosphinyl amines should also possess (S) configuration; 1-Phenylethylamine: W. Theilaker and H.-G. Winkler, Chem. Ber. 87, 691 (1954); 1,2,3,4-tetrahydro-1-naphthylamine: R. A. Smith, R. L. White, and A. Krantz, J. Med. Chem., 31, 1558 (1988); 1-Indanamine: H. E. Smith and T. C. Willis, Tetrahydron, 26, 107 (1970).
33. Free amines were assigned as (S) configuration by comparison of sign of optical rotation with literature value, and thusN-phosphinyl amines should also possess (S) configuration; 1-Phenylethylamine: W. Theilaker and H.-G. Winkler, Chem. Ber. 87, 691 (1954); 1,2,3,4-tetrahydro-1-naphthylamine: R. A. Smith, R. L. White, and A. Krantz, J. Med. Chem., 31, 1558 (1988); 1-Indanamine: H. E. Smith and T. C. Willis, Tetrahydron, 26, 107 (1970).
34. Free amines were assigned as (S) configuration by comparison of sign of optical rotation with literature value, and thusN-phosphinyl amines should also possess (S) configuration; 1-Phenylethylamine: W. Theilaker and H.-G. Winkler, Chem. Ber. 87, 691 (1954); 1,2,3,4-tetrahydro-1-naphthylamine: R. A. Smith, R. L. White, and A. Krantz, J. Med. Chem., 31, 1558 (1988); 1-Indanamine: H. E. Smith and T. C. Willis, Tetrahydron, 26, 107 (1970).
35. 3, and the mixture was continued to stir for 4 h at 0°C. The reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with diethyl ether. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and the excess solvents were removed under reduced pressure. The purification by column chromatography on silica gel (hexane / ethyl acetate / dichloromethane) gave 148.0 mg of the corresponding amine; 85% yield. The optical purity was determined by using Daicel Chiralpak AD (hexane / 2-propanol).