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Volumn 5, Issue 5, 1999, Pages 1544-1564

Trimerisation of the cationic fragments [(η-ring)M(Aa)]+ ((η-ring) M = (η5-C5Me5)Rh, (η5-C5Me5)Ir,(η6-p-MeC 6H4iPr)Ru; Aa = α-amino acidate) with chiral self-recognition: Synthesis, characterisation, solution studies and catalytic reactions of the trimers

Author keywords

Amino acids; Asymmetric catalysis; Iridium; Rhodium; Ruthenium

Indexed keywords

CATION;

EID: 0032898547     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19990503)5:5<1544::aid-chem1544>3.0.co;2-t     Document Type: Article
Times cited : (108)

References (97)
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    • The sequence rules establish the following priority order: η-ring > O quelate > O bridging > N. See: a) R. S. Cahn, C. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413, Angew. Chem. Int. Ed. Engl. 1966, 4, 385;
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    • The sequence rules establish the following priority order: η-ring > O quelate > O bridging > N. See: a) R. S. Cahn, C. Ingold, V. Prelog, Angew. Chem. 1966, 78, 413, Angew. Chem. Int. Ed. Engl. 1966, 4, 385;
    • (1966) Angew. Chem. Int. Ed. Engl. , vol.4 , pp. 385
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    • A detailed search of 'M(pro)' fragments in the CSD file showed all the structures to have identical chirality for the α-carbon and for the coordinated aminic nitrogen of the aminoacidate ligand. See also: a) R. D. Gillard, O. P. Slyudkin, J. Chem. Soc. Dalton Trans. 1978, 152;
    • (1978) J. Chem. Soc. Dalton Trans. , pp. 152
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    • note
    • Rh.
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    • note
    • For the D-prolinate compounds 7 the configurations at the carbon and nitrogen atoms are R. The configuration at the HC(OH) carbon of the 4-OH-L-prolinate complexes 9 is R and it is not quoted in the general descriptors.
  • 42
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    • note
    • 4 groups (B(3), F(1c)-F(4c)).
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    • note
    • 2O, and hydrocarbon solvents. Due to solubility reasons we were not able to carry out solution measurements for the following solvent/complex pairs : in dichloromethane, acetone, methanol, and water, compounds 1a, 2a, 9a, and 9b; in dichloromethane, methanol, and water, compounds 3a and 5a; in dichloromethane, compounds 1c, 3c, 4b, and 9c; in methanol and water, compound 3b and in water, compounds 4c and 5b.
  • 50
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    • note
    • 5 (rhodium and iridium trimers) or methyl arene protons (ruthenium derivatives) of each diastereomer. Error limits in each integral are estimated as ±2 %.
  • 51
    • 0347364368 scopus 로고    scopus 로고
    • note
    • The CD and some NOEDIFF spectra of the rhodium trimers are included as supplementary material.
  • 52
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    • note
    • Again, the L-prolinate complexes 6a,b behaved differently, the amount of the p diastereomer increasing with time.
  • 53
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    • note
    • Diastereomeric compositions for the iridium trimers 3b, 4b, 6b, and 8b are included in the supplementary material.
  • 56
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    • note
    • Surprisingly, the diastereomerisation of the iridium compound 8b in water was accompanied by partial deuteration of the N-Me amino acidate group. We have no satisfactory explanation for this.
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    • note
    • Obviously, for the D-prolinate compound 7c the corresponding enantiomers of the L-prolinate 6c were observed in each case, as assayed by CD spectroscopy.
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    • note
    • 0 the extrapolated equivalent conductance at zero concentration and c represents the equivalent concentration of the solution.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.