메뉴 건너뛰기




Volumn 130, Issue 7, 1997, Pages 989-1006

Preparative and Structural Chemistry of Diastereomeric Derivatives of 3-PhosphanylpyrroIidine and Their Palladium(II) Complexes -Asymmetric Grignard Cross-Coupling Reaction

Author keywords

Cooperative effects; Cross coupling; Grignard reactions; Nickel; Pyrrolidinephosphane

Indexed keywords


EID: 0039140464     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19971300729     Document Type: Article
Times cited : (20)

References (57)
  • 6
    • 0000383380 scopus 로고
    • A. Yamamoto, K. Tatsumi, S. Komiya, A. Nakamura, J. Am. Chem. Soc. 1984, 706, 8181 -8188; A. Yamamoto, T. Yamamoto, F. Osawa, Pure Appl. Chem. 1984, 56, 1621-1634; A. Yamamoto, T. Yamamoto, F. Osawa, Pure Appl. Chem. 1985,57, 1799-1808.
    • A. Yamamoto, K. Tatsumi, R. Hoffmann, J. K. Stille, Bull. Chew. Soc. Jpn. 1981, 54, 1857-1867; A. Yamamoto, K. Tatsumi, S. Komiya, A. Nakamura, J. Am. Chem. Soc. 1984, 706, 8181 -8188; A. Yamamoto, T. Yamamoto, F. Osawa, Pure Appl. Chem. 1984, 56, 1621-1634; A. Yamamoto, T. Yamamoto, F. Osawa, Pure Appl. Chem. 1985,57, 1799-1808.
    • (1981) Bull. Chew. Soc. Jpn. , vol.54 , pp. 1857-1867
    • Yamamoto, A.1    Tatsumi, K.2    Hoffmann, R.3    Stille, J.K.4
  • 11
    • 33745412649 scopus 로고    scopus 로고
    • The configuration on the phosphorus center of a PdI2 complex is described by e.g. (S,SMp)-12-Pd, the configuration on the phosphorus center of the ligand displaced from this complex is described by (S,RP)-12. The change of the Cahn, Ingold Prelog descriptor (SMP → RP) on going from the PdI2 complex to the ligand (same configuration on the phosphorus center) is due to this nomenclature.
    • The configuration on the phosphorus center of a PdI2 complex is described by e.g. (S,SMp)-12-Pd, the configuration on the phosphorus center of the ligand displaced from this complex is described by (S,RP)-12. The change of the Cahn, Ingold Prelog descriptor (SMP → RP) on going from the PdI2 complex to the ligand (same configuration on the phosphorus center) is due to this nomenclature.
  • 18
    • 0001338514 scopus 로고
    • G. L. Baker, S. J. Fritschel, J. R. Stille, J. K. Stille, J. Org. Chem. 1981, 46, 2954-2960 and 2960-2965; I. Ojima, T. Kogure, N. Yoda, J. Org. Chem. 1980, 45, 4728-4739; F. Leydendecker, D. Laucher, Nouv. J. Chim. 1985, 9, 13-19.
    • I. Ojima, T. Kogure, N. Yoda, J. Org. Chem. 1980, 45, 4728-4739; G. L. Baker, S. J. Fritschel, J. R. Stille, J. K. Stille, J. Org. Chem. 1981, 46, 2954-2960 and 2960-2965; I. Ojima, T. Kogure, N. Yoda, J. Org. Chem. 1980, 45, 4728-4739; F. Leydendecker, D. Laucher, Nouv. J. Chim. 1985, 9, 13-19.
    • (1980) J. Org. Chem. , vol.45 , pp. 4728-4739
    • Ojima, I.1    Kogure, T.2    Yoda, N.3
  • 32
    • 33745431131 scopus 로고    scopus 로고
    • J. Mack, Diplomarbeit, Eberhard! Karls Universität, Tübingen, 1995.
    • J. Mack, Diplomarbeit, Eberhard! Karls Universität, Tübingen, 1995.
  • 34
    • 5344275511 scopus 로고
    • and literature cited. VPC values, found for couplings to C-4 and C-2 carbon atoms in diastereomeric (S,Rp)-13, (S,Sp)-l3 ligands can be used for confomational studies'7". A large Jpc constant suggests a small dihedral angle between the lone electron pair and the carbon atom. From this rule combined with a study of molecular models we could unambiguously derive the correct configuration at the phosphorus center.
    • J. H. Nelson, Coord. Client. Rev. 1995,139, 245-280 and literature cited. VPC values, found for couplings to C-4 and C-2 carbon atoms in diastereomeric (S,Rp)-13, (S,Sp)-l3 ligands can be used for confomational studies'7". A large Jpc constant suggests a small dihedral angle between the lone electron pair and the carbon atom. From this rule combined with a study of molecular models we could unambiguously derive the correct configuration at the phosphorus center.
    • (1995) Coord. Client. Rev. , vol.139 , pp. 245-280
    • Nelson, J.H.1
  • 36
    • 0008451370 scopus 로고
    • and réf.'61 . With our PdI2 complexes an optimum optical yield of 10% ee is reached.
    • T. Hayashi, M. Konishi, M. Fukushima, K. Kanehira, T. Hioki, M. Kumada, J. Org. Client. 1983, 48, 2195-2202 and réf.'61 . With our PdI2 complexes an optimum optical yield of 10% ee is reached.
    • (1983) J. Org. Client. , vol.48 , pp. 2195-2202
    • Hayashi, T.1    Konishi, M.2    Fukushima, M.3    Kanehira, K.4    Hioki, T.5    Kumada, M.6
  • 37
    • 0000535353 scopus 로고
    • Angew. Client. Int. Ed. Engl. 1994, 33, 497-537.
    • A. Togni, L. M. Venanzi, Angew. Client. 1994, 106, 517-547; Angew. Client. Int. Ed. Engl. 1994, 33, 497-537.
    • (1994) Angew. Client. , vol.106 , pp. 517-547
    • Togni, A.1    Venanzi, L.M.2
  • 41
    • 33745385665 scopus 로고
    • K. Issleib, A. Kipke, Z. Anorg. Allg. Chem. 1980, 464, 176-186; M. M. Taqui Khan, A. P. Reddy, Polyhedron 1987,6,2009-2018.
    • J R. C. Taylor, G. R. Dobson, R. A. Kolodny, Inorg. Chem. 1968, 7, 1886-1890; K. Issleib, A. Kipke, Z. Anorg. Allg. Chem. 1980, 464, 176-186; M. M. Taqui Khan, A. P. Reddy, Polyhedron 1987,6,2009-2018.
    • (1968) Inorg. Chem. , vol.7 , pp. 1886-1890
    • Taylor, J.R.C.1    Dobson, G.R.2    Kolodny, R.A.3
  • 43
    • 0026072359 scopus 로고    scopus 로고
    • P. Heimbach, T. Bartik, L. Marko, H. G. Schulte, Chirality
    • P. Heimbach, T. Bartik, L. Marko, H. G. Schulte, Chirality 1991, 3, 324-330; P.
  • 44
    • 33745383833 scopus 로고    scopus 로고
    • Heimbach, H. Schenkluhn, Top. Curr. Chem. 1980, 92, 45-108.
    • Heimbach, H. Schenkluhn, Top. Curr. Chem. 1980, 92, 45-108.
  • 52
    • 33745333941 scopus 로고    scopus 로고
    • J Different chemical shifts and JPC values, assigned to each carbon atom are due to restricted rotation about the N-acyl bond (cf. réf." ). All I3C{'H}-NMR spectra were measured at 298 K.
    • J Different chemical shifts and JPC values, assigned to each carbon atom are due to restricted rotation about the N-acyl bond (cf. réf." ). All I3C{'H}-NMR spectra were measured at 298 K.
  • 53
    • 33745395174 scopus 로고    scopus 로고
    • Different chemical shifts and JPC values, assigned to each carbon atom are due to the diastereomeric mixture. They can be classed with each of the two diastereomers in those cases, when separation is feasible (tertiary phosphanes).
    • Different chemical shifts and JPC values, assigned to each carbon atom are due to the diastereomeric mixture. They can be classed with each of the two diastereomers in those cases, when separation is feasible (tertiary phosphanes).
  • 54
    • 33745381200 scopus 로고    scopus 로고
    • 1H}NMR (10Q.62 MHz, 298 K): 4 d for (C-2)-(C-4) [2 diastereomers, each with 2 rotamers (slow interconversion of rotamers on the NMR time scale)]. 13C{'H}NMR (62.9 MHz, 298 K): coalescence spectrum with broad resonances for (C-2)-(C-4). 13C{1H}NMR (20.15 MHz, 298 K): 2 d for (C-2)-(C-4) [2 diastereomers (fast interconversion of rotamers on the NMR time scale)].
    • 1H}NMR (10Q.62 MHz, 298 K): 4 d for (C-2)-(C-4) [2 diastereomers, each with 2 rotamers (slow interconversion of rotamers on the NMR time scale)]. 13C{'H}NMR (62.9 MHz, 298 K): coalescence spectrum with broad resonances for (C-2)-(C-4). 13C{1H}NMR (20.15 MHz, 298 K): 2 d for (C-2)-(C-4) [2 diastereomers (fast interconversion of rotamers on the NMR time scale)].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.