메뉴 건너뛰기




Volumn 73, Issue 16, 2008, Pages 6330-6340

Probing the importance of the hemilabile site of bis(phosphine) monoxide ligands in the copper-catalyzed addition of diethylzinc to N-phosphinoylimines: Discovery of new effective chiral ligands

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC SYSTEMS; CHEMICAL EQUATIONS; CHIRAL AMINES; CHIRAL LIGANDS; DIETHYL ZINC; NEW CLASS; NITROALKENES; PHOSPHINE OXIDES; PHOSPHINOYLIMINE;

EID: 50149091086     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800969x     Document Type: Article
Times cited : (77)

References (101)
  • 15
    • 85023767450 scopus 로고    scopus 로고
    • The Transition Metal Coordination Chemistry of Hemilabile Ligands
    • Karlin, K. D, Ed, Wiley: New York
    • (b) Slone, C. S.; Weinberger, D. A.; Mirkin, C. A. The Transition Metal Coordination Chemistry of Hemilabile Ligands. In Progres in Inorganic Chemistry; Karlin, K. D., Ed.; Wiley: New York, 1999; Vol. 48, pp 233-350.
    • (1999) Progres in Inorganic Chemistry , vol.48 , pp. 233-350
    • Slone, C.S.1    Weinberger, D.A.2    Mirkin, C.A.3
  • 20
    • 0000646546 scopus 로고    scopus 로고
    • For C=C groups, see: (c) Barthel-Rosa, L. P.; Maitra, K.; Nelson, J. H. Inorg. Chem. 1998, 37, 633.
    • For C=C groups, see: (c) Barthel-Rosa, L. P.; Maitra, K.; Nelson, J. H. Inorg. Chem. 1998, 37, 633.
  • 23
    • 50149106738 scopus 로고    scopus 로고
    • Abatjoglou, A. G.; Billig, E. U.S.Patent 4 522 933, 1985.
    • (a) Abatjoglou, A. G.; Billig, E. U.S.Patent 4 522 933, 1985.
  • 24
    • 50149083242 scopus 로고    scopus 로고
    • Abatjoglou, A. G.; Bryant, D. R. U.S.Patent 4 593 011, 1986.
    • (b) Abatjoglou, A. G.; Bryant, D. R. U.S.Patent 4 593 011, 1986.
  • 25
    • 50149089373 scopus 로고    scopus 로고
    • Oswald, A. A.; Jermasen, T. G.; Westner, A. A.; Huang, I. D. U.S.Patent 4 687 874, 1987.
    • (c) Oswald, A. A.; Jermasen, T. G.; Westner, A. A.; Huang, I. D. U.S.Patent 4 687 874, 1987.
  • 26
    • 50149112605 scopus 로고    scopus 로고
    • Argyropoulos, J. N.; Bryant, D. R.; Morrison, D. L.; Stockman, K. E.; Abatjoglou, A. G. U.S.Patent 5 932 772, 1999.
    • (d) Argyropoulos, J. N.; Bryant, D. R.; Morrison, D. L.; Stockman, K. E.; Abatjoglou, A. G. U.S.Patent 5 932 772, 1999.
  • 50
    • 33845281512 scopus 로고    scopus 로고
    • Monoxidation of diphosphine by copper has been reported: Berners-Price, S. J.; Johnson, R. K.; Mirabelli, C. K.; Faucette, L. F.; McCabe, F. L.; Sadler, P. J. Inorg. Chem. 1987, 26, 3383.
    • Monoxidation of diphosphine by copper has been reported: Berners-Price, S. J.; Johnson, R. K.; Mirabelli, C. K.; Faucette, L. F.; McCabe, F. L.; Sadler, P. J. Inorg. Chem. 1987, 26, 3383.
  • 51
    • 11144271344 scopus 로고    scopus 로고
    • 2Zn,-40 °C, 20 min) prior to the addition of the ligand. Hence, in the latter, the monoxidation of the diphosphine was slowed down.
    • 2Zn,-40 °C, 20 min) prior to the addition of the ligand. Hence, in the latter, the monoxidation of the diphosphine was slowed down.
  • 58
    • 1842430904 scopus 로고    scopus 로고
    • For a review on diphosphine monoxides, see
    • For a review on diphosphine monoxides, see: Grushin, V. V. Chem. Rev. 2004, 104, 1629.
    • (2004) Chem. Rev , vol.104 , pp. 1629
    • Grushin, V.V.1
  • 61
    • 50149086897 scopus 로고    scopus 로고
    • U.S. Patent 5 919 984
    • (b) Grushin, V. V. U.S. Patent 5 919 984, 1999.
    • (1999)
    • Grushin, V.V.1
  • 63
    • 33846550091 scopus 로고    scopus 로고
    • There are other methods reported for the monoxidation of diphosphines but these are either limited in scope or give low yields. For usual oxidants (O2, H2O2, Br2, see: (a) Bishop, J. J, Davison, A, Katcher, M. L, Lichtenberg, D. W, Merrill, R. E, Smart, J. C. J. Organomet. Chem. 1971, 27, 241
    • 2), see: (a) Bishop, J. J.; Davison, A.; Katcher, M. L.; Lichtenberg, D. W.; Merrill, R. E.; Smart, J. C. J. Organomet. Chem. 1971, 27, 241.
  • 67
    • 0000158123 scopus 로고    scopus 로고
    • 4/benzophenone (or MeOH), see: (e) Ninoreille, S.; Broussier, R.; Amardeil, R.; Kubicki, M. M.; Gautheron, B. Bull. Soc. Chim. Fr. 1995, 132, 128.
    • 4/benzophenone (or MeOH), see: (e) Ninoreille, S.; Broussier, R.; Amardeil, R.; Kubicki, M. M.; Gautheron, B. Bull. Soc. Chim. Fr. 1995, 132, 128.
  • 70
    • 50149091726 scopus 로고    scopus 로고
    • There is only one report from Mäding and Scheller for the monoxidation of a trialkyldiphosphine (dimethylphosphinoethane): Mädding, P.; Scheller, D. Z. Anorg. Allg. Chem. 1988, 567, 179.
    • There is only one report from Mäding and Scheller for the monoxidation of a trialkyldiphosphine (dimethylphosphinoethane): Mädding, P.; Scheller, D. Z. Anorg. Allg. Chem. 1988, 567, 179.
  • 72
    • 50149105881 scopus 로고    scopus 로고
    • (R)-Butiphane was kindly provided by Solvias AG.
    • (R)-Butiphane was kindly provided by Solvias AG.
  • 74
    • 50149111747 scopus 로고    scopus 로고
    • See Supporting Information for crystal structure of compounds 6 and 8
    • See Supporting Information for crystal structure of compounds 6 and 8.
  • 75
    • 50149090860 scopus 로고    scopus 로고
    • The deprotonation at the α position occurs syn to the P=O moiety.
    • The deprotonation at the α position occurs syn to the P=O moiety.
  • 77
    • 50149098549 scopus 로고
    • U.S. Patent 5 021 131
    • (b) Burk, M. J. U.S. Patent 5 021 131, 1991.
    • (1991)
    • Burk, M.J.1
  • 78
    • 50149111317 scopus 로고
    • U.S. Patent 5 171 892
    • (c) Burk, M. J. U.S. Patent 5 171 892, 1992.
    • (1992)
    • Burk, M.J.1
  • 79
    • 14644439830 scopus 로고    scopus 로고
    • The conditions modified from those reported by Dezfuli and Gooßen gave the desired compound: Goossen, L. J.; Dezfuli, M. K. Synlett 2005, 445.
    • The conditions modified from those reported by Dezfuli and Gooßen gave the desired compound: Goossen, L. J.; Dezfuli, M. K. Synlett 2005, 445.
  • 80
    • 50149119655 scopus 로고    scopus 로고
    • The reduction gave rise to a mixture of the starting material 33, the desired primary phosphine 34, compounds 41 and 42. If the temperature of the reaction mixture was allowed to rise above-40°C, additional compounds (43, 44) started to appear.
    • The reduction gave rise to a mixture of the starting material 33, the desired primary phosphine 34, compounds 41 and 42. If the temperature of the reaction mixture was allowed to rise above-40°C, additional compounds (43, 44) started to appear.
  • 83
    • 50149109593 scopus 로고    scopus 로고
    • See ref 7
    • (a) See ref 7.
  • 86
    • 50149101513 scopus 로고    scopus 로고
    • Ligands 17 and 18 could promote the addition of diethylzinc to 1 without the involvement of copper species.
    • Ligands 17 and 18 could promote the addition of diethylzinc to 1 without the involvement of copper species.
  • 87
    • 0033802083 scopus 로고    scopus 로고
    • Coordination between copper and a phenyl ring has already been observed: Hubig, S. M.; Lindeman, S. V.; Kochi, J. K. Coord. Chem. Rev. 2000, 200-202, 831.
    • Coordination between copper and a phenyl ring has already been observed: Hubig, S. M.; Lindeman, S. V.; Kochi, J. K. Coord. Chem. Rev. 2000, 200-202, 831.
  • 91
    • 50149096806 scopus 로고    scopus 로고
    • 2Zn, see: (a) Alexakis, A. Asymmetric Conjugate Addition. In Organocopper Reagents: A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, 1994; pp 159-183.
    • 2Zn, see: (a) Alexakis, A. Asymmetric Conjugate Addition. In Organocopper Reagents: A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, 1994; pp 159-183.
  • 92
    • 0004246896 scopus 로고    scopus 로고
    • Krause, N, Ed, Wiley-VCH: Weinheim, Germany
    • (b) Modern Organocopper Chemistry; Krause, N., Ed.; Wiley-VCH: Weinheim, Germany, 2002.
    • (2002) Modern Organocopper Chemistry
  • 93
  • 95
    • 50149119224 scopus 로고    scopus 로고
    • It has been previously demonstrated that the reaction follows a first-order kinetics in catalyst, see ref 18
    • (a) It has been previously demonstrated that the reaction follows a first-order kinetics in catalyst, see ref 18.
  • 97
    • 50149092617 scopus 로고    scopus 로고
    • Presented in the Experimental Section are the experimental procedures and spectral data for the new ligands 10 and 16a,b and their intermediates. Complete experimental procedures and spectral data for all new compounds are presented in the Supporting Information
    • Presented in the Experimental Section are the experimental procedures and spectral data for the new ligands 10 and 16a,b and their intermediates. Complete experimental procedures and spectral data for all new compounds are presented in the Supporting Information.
  • 98
    • 0025280171 scopus 로고    scopus 로고
    • This material was synthesized according to the literature procedure: Berridge, M. S, Franceschini, M. P, Rosenfeld, E, Tewson, T. J. J. Org. Chem. 1990, 55, 1211
    • This material was synthesized according to the literature procedure: Berridge, M. S.; Franceschini, M. P.; Rosenfeld, E.; Tewson, T. J. J. Org. Chem. 1990, 55, 1211.
  • 99
    • 0000136461 scopus 로고    scopus 로고
    • This material was synthesized according to the literature procedure: Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518
    • This material was synthesized according to the literature procedure: Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518.
  • 100
    • 84994437953 scopus 로고    scopus 로고
    • This material was synthesized according to the literature procedure: Casalnuovo, A. L, RajanBabu, T. V, Ayers, T. A, Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869
    • This material was synthesized according to the literature procedure: Casalnuovo, A. L.; RajanBabu, T. V.; Ayers, T. A.; Warren, T. H. J. Am. Chem. Soc. 1994, 116, 9869.
  • 101
    • 85026866527 scopus 로고    scopus 로고
    • This material was synthesized according to the literature procedure; Desrosiers, J.-N, Côté, A, Boezio, A. A, Charette, A. B. Org. Synth. 2006, 83, 5
    • This material was synthesized according to the literature procedure; Desrosiers, J.-N.; Côté, A.; Boezio, A. A.; Charette, A. B. Org. Synth. 2006, 83, 5.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.