메뉴 건너뛰기




Volumn 6, Issue 7, 2000, Pages 1127-1139

Stereoselectivity and chiral recognition in copper(I) olefin complexes with a chiral diamine

Author keywords

Chiral diamine; Chirality; Copper; Enantioselectivity; Olefin

Indexed keywords

ALKENE DERIVATIVE; COPPER COMPLEX; DIAMINE;

EID: 0034599378     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000403)6:7<1127::AID-CHEM1127>3.3.CO;2-X     Document Type: Article
Times cited : (46)

References (70)
  • 2
    • 0030893497 scopus 로고    scopus 로고
    • J. A. Gladysz, B. J. Boone, Angew. Chem. 1997, 109, 566; Angew. Chem. Int. Ed. Engl. 1997, 36, 550.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 550
  • 5
    • 0009350202 scopus 로고
    • A paradigmatic case is the homogeneous rhodium-catalyzed asymmetric hydrogenation. See J. M. Brown, Chem. Soc. Rev. 1993, 25.
    • (1993) Chem. Soc. Rev. , pp. 25
    • Brown, J.M.1
  • 6
    • 0001754175 scopus 로고    scopus 로고
    • For example trigonal copper(I) olefin complexes such as those described in this paper might serve as steric models of the palladium(0) intermediates following the transition state of asymmetric allylic alkylation. See: a) S. Ramdeehul, P. Dierkes, R. Aquado, P. C. Kamer, P. W. N. M. van Leeuwen, J. A. Osborn, Angew. Chem. 1998, 110, 3302; Angew. Chem. Int. Ed. 1998, 37, 3118; b) E. Peña-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Åkermark, P. Elquist, J. Am. Chem. Soc. 1996, 118, 4299.
    • (1998) Angew. Chem. , vol.110 , pp. 3302
    • Ramdeehul, S.1    Dierkes, P.2    Aquado, R.3    Kamer, P.C.4    Van Leeuwen, P.W.N.M.5    Osborn, J.A.6
  • 7
    • 0032484249 scopus 로고    scopus 로고
    • For example trigonal copper(I) olefin complexes such as those described in this paper might serve as steric models of the palladium(0) intermediates following the transition state of asymmetric allylic alkylation. See: a) S. Ramdeehul, P. Dierkes, R. Aquado, P. C. Kamer, P. W. N. M. van Leeuwen, J. A. Osborn, Angew. Chem. 1998, 110, 3302; Angew. Chem. Int. Ed. 1998, 37, 3118; b) E. Peña-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Åkermark, P. Elquist, J. Am. Chem. Soc. 1996, 118, 4299.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 3118
  • 8
    • 0343136162 scopus 로고    scopus 로고
    • For example trigonal copper(I) olefin complexes such as those described in this paper might serve as steric models of the palladium(0) intermediates following the transition state of asymmetric allylic alkylation. See: a) S. Ramdeehul, P. Dierkes, R. Aquado, P. C. Kamer, P. W. N. M. van Leeuwen, J. A. Osborn, Angew. Chem. 1998, 110, 3302; Angew. Chem. Int. Ed. 1998, 37, 3118; b) E. Peña-Cabrera, P.-O. Norrby, M. Sjögren, A. Vitagliano, V. De Felice, J. Oslob, S. Ishii, D. O'Neill, B. Åkermark, P. Elquist, J. Am. Chem. Soc. 1996, 118, 4299.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 4299
    • Peña-Cabrera, E.1    Norrby, P.-O.2    Sjögren, M.3    Vitagliano, A.4    De Felice, V.5    Oslob, J.6    Ishii, S.7    O'Neill, D.8    Åkermark, B.9    Elquist, P.10
  • 10
  • 12
    • 0029954622 scopus 로고    scopus 로고
    • b) M. S. Visser, J. P. A. Harrity, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 3779; J. P. Morken, M. T. Didiuk, M. S. Visser, A. H. Hoveyda, J. Am. Chem. Soc. 1994, 116, 3123; M. Kitamura, I. Kasahara, K. Manabe, R. Noyori, H. Takaya, J. Org. Chem. 1988, 53, 708.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3779
    • Visser, M.S.1    Harrity, J.P.A.2    Hoveyda, A.H.3
  • 13
    • 0000365809 scopus 로고
    • b) M. S. Visser, J. P. A. Harrity, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 3779; J. P. Morken, M. T. Didiuk, M. S. Visser, A. H. Hoveyda, J. Am. Chem. Soc. 1994, 116, 3123; M. Kitamura, I. Kasahara, K. Manabe, R. Noyori, H. Takaya, J. Org. Chem. 1988, 53, 708.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 3123
    • Morken, J.P.1    Didiuk, M.T.2    Visser, M.S.3    Hoveyda, A.H.4
  • 14
    • 33845278869 scopus 로고
    • b) M. S. Visser, J. P. A. Harrity, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 3779; J. P. Morken, M. T. Didiuk, M. S. Visser, A. H. Hoveyda, J. Am. Chem. Soc. 1994, 116, 3123; M. Kitamura, I. Kasahara, K. Manabe, R. Noyori, H. Takaya, J. Org. Chem. 1988, 53, 708.
    • (1988) J. Org. Chem. , vol.53 , pp. 708
    • Kitamura, M.1    Kasahara, I.2    Manabe, K.3    Noyori, R.4    Takaya, H.5
  • 16
    • 0001129207 scopus 로고    scopus 로고
    • See for example: a) A. Carmona, A. Corma, M. Iglesias, F. Sánchez, Inorg. Chim. Acta 1996, 244, 239; b) P. J. Pérez, M. Brookhart, J. L. Templeton, Organometallics 1993, 12, 261; c) Z. Li, R. W. Quan, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5889.
    • (1996) Inorg. Chim. Acta , vol.244 , pp. 239
    • Carmona, A.1    Corma, A.2    Iglesias, M.3    Sánchez, F.4
  • 17
    • 0001022701 scopus 로고
    • See for example: a) A. Carmona, A. Corma, M. Iglesias, F. Sánchez, Inorg. Chim. Acta 1996, 244, 239; b) P. J. Pérez, M. Brookhart, J. L. Templeton, Organometallics 1993, 12, 261; c) Z. Li, R. W. Quan, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5889.
    • (1993) Organometallics , vol.12 , pp. 261
    • Pérez, P.J.1    Brookhart, M.2    Templeton, J.L.3
  • 18
    • 0000072415 scopus 로고
    • See for example: a) A. Carmona, A. Corma, M. Iglesias, F. Sánchez, Inorg. Chim. Acta 1996, 244, 239; b) P. J. Pérez, M. Brookhart, J. L. Templeton, Organometallics 1993, 12, 261; c) Z. Li, R. W. Quan, E. N. Jacobsen, J. Am. Chem. Soc. 1995, 117, 5889.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5889
    • Li, Z.1    Quan, R.W.2    Jacobsen, E.N.3
  • 26
    • 5544240942 scopus 로고    scopus 로고
    • note
    • The diamine 1 was always used in almost enantiomerically pure form. It was prepared and resolved by us and both (S,S)-1 and (R,R)-1 enantiomers were available. Most experiments were performed using (S,S)-1 but in some cases the R, R enantiomer was used. To avoid confusion in presenting the results, throughout this paper we consistently refer to the use of (S,S)-1.
  • 27
    • 5544228515 scopus 로고    scopus 로고
    • note
    • Although allowed by symmetry, the alternate possibility, S, S, S, S, is too unlikely on steric grounds to be considered as the configuration of a major species.
  • 35
    • 5544221493 scopus 로고    scopus 로고
    • note
    • 2+ ion were present.
  • 36
    • 5544228509 scopus 로고    scopus 로고
    • note
    • Confusion should be avoided by keeping in mind that according to the re-si nomenclature convention, a formal inversion takes place in going from propene to any higher α-olefin. That is, the same enantioface that is named re in the propene molecule, is named si in the case of higher olefins and vice-versa.
  • 40
    • 5544258607 scopus 로고    scopus 로고
    • note
    • 2, respectively, while in the platinum complex the corresponding distance is 4.2 Å.
  • 41
    • 5544326718 scopus 로고    scopus 로고
    • note
    • A further decrease in stability of the asymmetric R, S, S, S configuration is observed in the case of allylic alcohols and ethers (see Table 1) and can also be rationalized. Since in this arrangement the copper ion is hindered on one side of the coordination plane, the interactions with the counterion or solvent on the "open" side should be stronger, thus leaving less room for the intramolecular interaction with the alcoholic oxygen and reducing the overall relative stability compared with the symmetric configuration R, S, S, R.
  • 42
    • 5544244952 scopus 로고    scopus 로고
    • note
    • Hydrogen bonding between the OH group and the counterion (possibly occurring in close-tight ion pairs) is not relevant for the chiral recognition of the R enantiomer, since substitution of a methoxy group for the oxydryl in the 3-methoxy-1-butene complex 10 did not affect the selectivity.
  • 43
    • 5544303986 scopus 로고    scopus 로고
    • note
    • -1 above 8a. This is in quantitative disagreement with the experiment but can be explained in the same way as the propene case (see also reference [25]).
  • 44
    • 5544247855 scopus 로고    scopus 로고
    • See reference [2a], p. 69
    • See reference [2a], p. 69.
  • 48
    • 0003633339 scopus 로고
    • College Station, TX, and Enraf-Nonius, Delft, The Netherlands
    • B. A. Frenz & Associates Inc. Structure Determination Package (SDP), College Station, TX, and Enraf-Nonius, Delft, The Netherlands, 1982.
    • (1982) Structure Determination Package (SDP)
    • Frenz, B.A.1
  • 58
    • 0003744120 scopus 로고    scopus 로고
    • Vrije Universiteit Amsterdam: Amsterdam. The Netherlands
    • ADF 2.3.0, Vrije Universiteit Amsterdam: Amsterdam. The Netherlands, 1996.
    • (1996) ADF 2.3.0


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.