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Volumn 28, Issue 7, 2009, Pages 2001-2004

Diastereoselective bis-cyclopalladation of ferrocene-1,1 -diyl bis-imidazolines: Translation of central via axial into planar chirality

Author keywords

[No Author keywords available]

Indexed keywords

AZA-CLAISEN REARRANGEMENTS; BIS-IMIDAZOLINES; C - H ACTIVATIONS; CHELATE COMPLEXES; CYCLOPALLADATION; DIASTEREOSELECTIVE; FERROCENE; MICHAEL ADDITIONS; PALLADACYCLE; PLANAR CHIRALITIES; REACTIVE PRECURSORS;

EID: 65349160879     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900137c     Document Type: Article
Times cited : (51)

References (47)
  • 7
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    • Only few direct diastereoselective monocyclopalladations of chiral ferrocenes are known: (a) Kuz'min, L. G.; Struchkov, Y. T.; Troitskaya, L. L.; Sokolov, V. I.: Reutov, O. A. IZv. Akad. Nauk SSSR, Ser. Khim. 1979, 1528.
    • Only few direct diastereoselective monocyclopalladations of chiral ferrocenes are known: (a) Kuz'min, L. G.; Struchkov, Y. T.; Troitskaya, L. L.; Sokolov, V. I.: Reutov, O. A. IZv. Akad. Nauk SSSR, Ser. Khim. 1979, 1528.
  • 10
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    • Zhao, G.: Wang, Q.-G.; Mak, T. C. W. Tetrahedron: Asymmetry 1998, 9, 1557. (dd) Zhao, G.; Wang, Q.-G.; Mak, T. C. W. Organometallics 1998, 17, 3437.
    • (d) Zhao, G.: Wang, Q.-G.; Mak, T. C. W. Tetrahedron: Asymmetry 1998, 9, 1557. (dd) Zhao, G.; Wang, Q.-G.; Mak, T. C. W. Organometallics 1998, 17, 3437.
  • 13
    • 0037164642 scopus 로고    scopus 로고
    • Previous syntheses of nonracemic ferrocenyl bis-palladacycles relied on double ortho-lithiation, iodination, and subsequent oxidative addition of Pd(0) to the corresponding bis-iodoferrocenes: Kang, J.; Yew, K. H.; Kim, T. H.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509.
    • Previous syntheses of nonracemic ferrocenyl bis-palladacycles relied on double ortho-lithiation, iodination, and subsequent oxidative addition of Pd(0) to the corresponding bis-iodoferrocenes: Kang, J.; Yew, K. H.; Kim, T. H.; Choi, D. H. Tetrahedron Lett. 2002, 43, 9509.
  • 14
    • 42149137722 scopus 로고
    • The stereodescriptors with regard to the planar chirality are used according to: Schlögl, K
    • p indicates the configuration of a bottom Cp,while an asterisk indicates a second ferrocene unit
    • p indicates the configuration of a bottom Cp,while an asterisk indicates a second ferrocene unit.
    • (1967) Top. Stereochem , vol.1 , pp. 39
  • 15
    • 65349147338 scopus 로고    scopus 로고
    • The seven diastereomers would have the following configurations: S p,S p,S* p, S * p, Rp, S p, S * p, S* p, R p, R p, S* p, S * p, Rp, Sp, R * p, S * p, R p, S p, S* p, R * p, Rp, R p, R* p,S* p, and RpR p, R* p, R*p
    • p
  • 16
    • 33644634815 scopus 로고    scopus 로고
    • Application of Pd chelate complexes with ferrocene bis-oxazolines to Suzuki and Heck couplings: Lee, S
    • Application of Pd chelate complexes with ferrocene bis-oxazolines to Suzuki and Heck couplings: Lee, S. J. Organomet. Chem. 2006, 691, 1347.
    • (2006) J. Organomet. Chem , vol.691 , pp. 1347
  • 17
    • 65349165996 scopus 로고    scopus 로고
    • Recent review about applications of ferroeenes in asymmetric catalvsis
    • Recent review about applications of ferroeenes in asymmetric catalvsis: Arrayás, R. G.; Adrio. J.; Carretero, J. C. Angew. Chem., Int. Ed. 2006, 45, 1614.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 1614
    • Arrayás, R.G.1    Adrio, J.2    Carretero, J.C.3
  • 18
    • 65349099056 scopus 로고    scopus 로고
    • Crystallographic data for 3 have been deposited as Supporting Information and with the Cambridge Crystallographic Data Centre as deposition number 721052; the material is available free of charge via the Internet at http://www.ccdc.cam.ac.uk/products/csd/request/.
    • Crystallographic data for 3 have been deposited as Supporting Information and with the Cambridge Crystallographic Data Centre as deposition number 721052; the material is available free of charge via the Internet at http://www.ccdc.cam.ac.uk/products/csd/request/.
  • 19
    • 65349181703 scopus 로고    scopus 로고
    • Note that 3 is not only axially chiral but also pseudoplanar chiral due to the rigid conformation
    • Note that 3 is not only axially chiral but also pseudoplanar chiral due to the rigid conformation.
  • 20
    • 65349141509 scopus 로고    scopus 로고
    • The pyramidality at a given atom can be expressed by the difference between 360° and the sum of the three bond angles at that atom. For the present analysis, corresponding values at the sulfonylated N atoms are 9° (upper Cp in 3 as depicted in Figure 1) and 0° (lower Cp).
    • The pyramidality at a given atom can be expressed by the difference between 360° and the sum of the three bond angles at that atom. For the present analysis, corresponding values at the sulfonylated N atoms are 9° (upper Cp in 3 as depicted in Figure 1) and 0° (lower Cp).
  • 22
    • 65349183162 scopus 로고    scopus 로고
    • Crystallographic data for 4 have been deposited as Supporting Information and with the Cambridge Crystallographic Data Centre as deposition number 720443, is available free of charge via the Internet at
    • Crystallographic data for 4 have been deposited as Supporting Information and with the Cambridge Crystallographic Data Centre as deposition number 720443. This material is available free of charge via the Internet at http://www.ccdc.cam.ac.uk/products/csd/request/.
    • This material
  • 23
    • 65349140332 scopus 로고    scopus 로고
    • The pyramidality is 10° see ref 13
    • The pyramidality is 10° see ref 13.
  • 29
    • 26444441381 scopus 로고    scopus 로고
    • 2: Davies, D. L.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem. Soc. 2005, 127, 13754.
    • 2: Davies, D. L.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem. Soc. 2005, 127, 13754.
  • 37
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    • Bedford, R. B.; Cazin, C. S. 1; Holder, D. Coord. Chem. Rev. 2004, 248, 2283.
    • (g) Bedford, R. B.; Cazin, C. S. 1; Holder, D. Coord. Chem. Rev. 2004, 248, 2283.
  • 42
    • 65349123812 scopus 로고    scopus 로고
    • Interestingly, the MS spectra (MALDI) of 4 already indicated the formation of 6 in larger quantities during the measurement, while only traces of 6 were observed in the MS spectra of 3.
    • Interestingly, the MS spectra (MALDI) of 4 already indicated the formation of 6 in larger quantities during the measurement, while only traces of 6 were observed in the MS spectra of 3.
  • 47
    • 65349107400 scopus 로고    scopus 로고
    • p-configured bis-palladacycle might not be able to form a stable dimer but is still prone to protonolysis.
    • p-configured bis-palladacycle might not be able to form a stable dimer but is still prone to protonolysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.