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Volumn , Issue 5, 2002, Pages 752-758

Mechanistic aspects of hydrogen addition during enantioselective rhodium-catalysed reduction of C=C double bonds with formic acid/triethylamine or molecular hydrogen

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; DEUTERIUM; HYDROGENATION; ISOMERIZATION; RHODIUM; SYNTHESIS (CHEMICAL);

EID: 0036026544     PISSN: 1470479X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (16)

References (33)
  • 14
    • 0032839379 scopus 로고    scopus 로고
    • For a related study on heterogeneously Pd-catalysed transfer hydrogenation, see (a) J. Yu and J. B. Spencer, Chem. Commun., 1998, 1935; (b) J. Yu and J. B. Spencer, Chem. Eur. J., 1999, 5, 2237.
    • (1998) Chem. Commun. , pp. 1935
    • Yu, J.1    Spencer, J.B.2
  • 15
    • 0032839379 scopus 로고    scopus 로고
    • For a related study on heterogeneously Pd-catalysed transfer hydrogenation, see (a) J. Yu and J. B. Spencer, Chem. Commun., 1998, 1935; (b) J. Yu and J. B. Spencer, Chem. Eur. J., 1999, 5, 2237. B. T. Khai and A. Arcelli, J. Org. Chem., 1989, 54, 949.
    • (1999) Chem. Eur. J. , vol.5 , pp. 2237
    • Yu, J.1    Spencer, J.B.2
  • 17
    • 67049108133 scopus 로고    scopus 로고
    • note
    • Enantioselectivities of up to 94% can be achieved with in-situ-formed Rh/bppm catalysts under optimised conditions.
  • 18
    • 67049118376 scopus 로고    scopus 로고
    • manuscript in preparation
    • Details of the NMR spectroscopic assignment will be given separately, S. Lange, W. Leitner, R. Mynott and C. Wirtz, manuscript in preparation.
    • Lange, S.1    Leitner, W.2    Mynott, R.3    Wirtz, C.4
  • 19
    • 84970609647 scopus 로고
    • 13C-NMR spectroscopy in deuterium labelling studies, see (a) J. M. Brown, A. E. Derome, G. D. Hughes and P. K. Monaghan, Aust. J. Chem., 1992, 45, 143; (b) J. K. MacDougall, M. C. Simpson and D. J. Cole-Hamilton, J. Chem. Soc., Dalton Trans., 1994, 3061.
    • (1992) Aust. J. Chem. , vol.45 , pp. 143
    • Brown, J.M.1    Derome, A.E.2    Hughes, G.D.3    Monaghan, P.K.4
  • 22
    • 67049088910 scopus 로고    scopus 로고
    • note
    • 2 pressure.
  • 25
    • 67049169520 scopus 로고    scopus 로고
    • note
    • The major exception are catalysts with chiral ligands forming five-membered chelates, as the corresponding rhodium complexes are not e3ective for the formyl C-H bond cleavage.
  • 28
    • 67049096875 scopus 로고    scopus 로고
    • note
    • An alternative explanation involving rhodacylobutane intermediates was put forward to rationalise the change of vicinal to 1,3-addition during transfer hydrogenation of 1a or 1b in aqueous media. Although we cannot rule out this possibility, it does not provide a satisfactory explanation for the decisive influence of the allylic carboxyl group and the preferred incorporation of protons at C-1.
  • 33
    • 67049173297 scopus 로고    scopus 로고
    • note
    • Acidic hydrolysis proved less suitable. Control experiments showed that no measureable H/D exchange in product 5 occurred under the basic conditions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.