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Volumn , Issue 10, 2002, Pages 2569-2586

Iridium-catalysed allylic substitution: Stereochemical aspects and isolation of IrIII complexes related to the catalytic cycle

Author keywords

Allyl complexes; Allylic substitution; Asymmetric catalysis; Iridium; NMR spectroscopy

Indexed keywords

ALKYLATION; ALLYLATION; CATALYSIS; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; LIGANDS; SPECTROSCOPIC ANALYSIS; SUBSTITUTION REACTIONS;

EID: 0036788408     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0682(200210)2002:10<2569::AID-EJIC2569>3.0.CO;2-5     Document Type: Article
Times cited : (150)

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    • For characterised σ- and π-allyl complexes see: [8a] K. D. John, K. V. Salazar, B. L. Scott, R. T. Baker, A. P. Sattelberger, Chem. Commun. 2000, 581-582. [8b] K. D. John, K. V. Salazar, B. L. Scott, R. T Baker, A. P. Sattelberger, Organometallics 2001, 2, 296-304. [8c] J. B. Wakefield, J. M. Stryker, Organometallics 1990, 9, 2428-2430. [8d] C. S. Chin, D. Chong, S. Lee, Y. J. Park, Organometallics 2000, 19, 4043-4050. [8e] T. H. Tulip, J. A. Ibers, J. Am. Chem. Soc. 1979, 101, 4201-4212. [8f] E. L. Muetterties, K. D. Tau, J. F. Kirner, T. V. Harris, J. Stark, M. R. Thompson, V. W. Day, Organometallics 1982, 1, 1562-1567. [8g] J. Müller, B. Passon, J. A. Pickardt, J. Organomet. Chem. 1982, 236, C11-C14. [8h] P. Powell, J. Organomet. Chem. 1983, 252, 205-208. [8i] O. Boutry, E. Gutiérrez, A. Monge, M. C. Nicasio, P. J. Pérez, E. Carmona, J. Am. Chem. Soc. 1992, 114, 7288-7290.
    • (1982) Organometallics , vol.1 , pp. 1562-1567
    • Muetterties, E.L.1    Tau, K.D.2    Kirner, J.F.3    Harris, T.V.4    Stark, J.5    Thompson, M.R.6    Day, V.W.7
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    • For characterised σ- and π-allyl complexes see: [8a] K. D. John, K. V. Salazar, B. L. Scott, R. T. Baker, A. P. Sattelberger, Chem. Commun. 2000, 581-582. [8b] K. D. John, K. V. Salazar, B. L. Scott, R. T Baker, A. P. Sattelberger, Organometallics 2001, 2, 296-304. [8c] J. B. Wakefield, J. M. Stryker, Organometallics 1990, 9, 2428-2430. [8d] C. S. Chin, D. Chong, S. Lee, Y. J. Park, Organometallics 2000, 19, 4043-4050. [8e] T. H. Tulip, J. A. Ibers, J. Am. Chem. Soc. 1979, 101, 4201-4212. [8f] E. L. Muetterties, K. D. Tau, J. F. Kirner, T. V. Harris, J. Stark, M. R. Thompson, V. W. Day, Organometallics 1982, 1, 1562-1567. [8g] J. Müller, B. Passon, J. A. Pickardt, J. Organomet. Chem. 1982, 236, C11-C14. [8h] P. Powell, J. Organomet. Chem. 1983, 252, 205-208. [8i] O. Boutry, E. Gutiérrez, A. Monge, M. C. Nicasio, P. J. Pérez, E. Carmona, J. Am. Chem. Soc. 1992, 114, 7288-7290.
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    • Müller, J.1    Passon, B.2    Pickardt, J.A.3
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    • For characterised σ- and π-allyl complexes see: [8a] K. D. John, K. V. Salazar, B. L. Scott, R. T. Baker, A. P. Sattelberger, Chem. Commun. 2000, 581-582. [8b] K. D. John, K. V. Salazar, B. L. Scott, R. T Baker, A. P. Sattelberger, Organometallics 2001, 2, 296-304. [8c] J. B. Wakefield, J. M. Stryker, Organometallics 1990, 9, 2428-2430. [8d] C. S. Chin, D. Chong, S. Lee, Y. J. Park, Organometallics 2000, 19, 4043-4050. [8e] T. H. Tulip, J. A. Ibers, J. Am. Chem. Soc. 1979, 101, 4201-4212. [8f] E. L. Muetterties, K. D. Tau, J. F. Kirner, T. V. Harris, J. Stark, M. R. Thompson, V. W. Day, Organometallics 1982, 1, 1562-1567. [8g] J. Müller, B. Passon, J. A. Pickardt, J. Organomet. Chem. 1982, 236, C11-C14. [8h] P. Powell, J. Organomet. Chem. 1983, 252, 205-208. [8i] O. Boutry, E. Gutiérrez, A. Monge, M. C. Nicasio, P. J. Pérez, E. Carmona, J. Am. Chem. Soc. 1992, 114, 7288-7290.
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    • Powell, P.1
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    • For characterised σ- and π-allyl complexes see: [8a] K. D. John, K. V. Salazar, B. L. Scott, R. T. Baker, A. P. Sattelberger, Chem. Commun. 2000, 581-582. [8b] K. D. John, K. V. Salazar, B. L. Scott, R. T Baker, A. P. Sattelberger, Organometallics 2001, 2, 296-304. [8c] J. B. Wakefield, J. M. Stryker, Organometallics 1990, 9, 2428-2430. [8d] C. S. Chin, D. Chong, S. Lee, Y. J. Park, Organometallics 2000, 19, 4043-4050. [8e] T. H. Tulip, J. A. Ibers, J. Am. Chem. Soc. 1979, 101, 4201-4212. [8f] E. L. Muetterties, K. D. Tau, J. F. Kirner, T. V. Harris, J. Stark, M. R. Thompson, V. W. Day, Organometallics 1982, 1, 1562-1567. [8g] J. Müller, B. Passon, J. A. Pickardt, J. Organomet. Chem. 1982, 236, C11-C14. [8h] P. Powell, J. Organomet. Chem. 1983, 252, 205-208. [8i] O. Boutry, E. Gutiérrez, A. Monge, M. C. Nicasio, P. J. Pérez, E. Carmona, J. Am. Chem. Soc. 1992, 114, 7288-7290.
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    • Boutry, O.1    Gutiérrez, E.2    Monge, A.3    Nicasio, M.C.4    Pérez, P.J.5    Carmona, E.6
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    • note
    • Fast polymerization of aldehyde 5e prevented the preparation of acetate (E)-2e.
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    • For a study of the influence of donor capacity of ligands on the stability of (allyl)Rh complexes see: [16a] H. C. Volger, K. Vrieze, J. Organomet. Chem. 1967, 9, 527-536. [16b] H. C. Volger, K. Vrieze, J. Organomet. Chem. 1967, 9, 537-548.
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    • For a study of the influence of donor capacity of ligands on the stability of (allyl)Rh complexes see: [16a] H. C. Volger, K. Vrieze, J. Organomet. Chem. 1967, 9, 527-536. [16b] H. C. Volger, K. Vrieze, J. Organomet. Chem. 1967, 9, 537-548.
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    • note
    • 3 (0.02 mmol) in THF (4 mL). After 3 h at room temperature and a further 15 h under reflux, the reaction mixture was worked up.
  • 69
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    • and references therein
    • Trans influence or "transphobia" can strongly affect the stability and reactivity of organometallic compounds. See for example: J. Vicente, J. A. Abad, A. D. Frankland, M. C. Ramirez de Arellano, Chem. Eur. J. 1999, 5, 3066-3075 and references therein.
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    • Vicente, J.1    Abad, J.A.2    Frankland, A.D.3    Ramirez de Arellano, M.C.4
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    • Kazmeier, U.1    Zumpe, F.L.2
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    • O'Connor, J.M.1
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    • note
    • The terms endo and exo are defined in Scheme 10.
  • 102
    • 85163223578 scopus 로고    scopus 로고
    • note
    • R(S), 22.6 min.
  • 105
    • 0348222991 scopus 로고
    • Compound 11e was prepared previously by another route: M. F. Shostakovskii, N. V. Kuznetsov; Y. B. Zaretskaya, Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Trans.) 1963, 830-831; Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 1963, 922-923.
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    • A different synthesis for compound 10f was first described by: E. Eliel, L. Giza, A. Chester, J. Org. Chem. 1968, 33, 3754-3758.
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    • Eliel, E.1    Giza, L.2    Chester, A.3


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