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Volumn 4, Issue 1, 2006, Pages 41-43

Asymmetric allylic oxidation reactions catalyzed by a chiral nonracemic and C2-symmetric 2,2′-bipyridyl copper(i) complex

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CATALYSTS; COPPER COMPOUNDS; OLEFINS; OXIDATION; SOLVENTS;

EID: 33645683884     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b513374m     Document Type: Article
Times cited : (16)

References (22)
  • 2
    • 15044357098 scopus 로고    scopus 로고
    • For reviews on the synthesis and applications of chiral nonracemic 2,2′-bipyridines and 1,10-phenanthrolines, see:
    • M. P. A. Lyle N. D. Draper P. D. Wilson Org. Lett. 2005 7 901
    • (2005) Org. Lett. , vol.7 , pp. 901
    • Lyle, M.P.A.1    Draper, N.D.2    Wilson, P.D.3
  • 5
    • 0141955242 scopus 로고    scopus 로고
    • For discussions on the coordination chemistry of 2,2′-bipyridines and 1,10-phenanthrolines, see:
    • A. V. Malkov P. Koovský Curr. Org. Chem. 2003 7 1737
    • (2003) Curr. Org. Chem. , vol.7 , pp. 1737
    • Malkov, A.V.1    Koovský, P.2
  • 6
    • 0003625968 scopus 로고
    • G. Wilkinson, R. D. Gillard and J. A. McCleverty, Pergamon Press, Oxford, pp. 73-98
    • J. Reedijk, in Comprehensive Coordination Chemistry, ed., G. Wilkinson, R. D. Gillard, and, J. A. McCleverty, Pergamon Press, Oxford, 1987, vol. 2, pp. 73-98
    • (1987) Comprehensive Coordination Chemistry, Ed.
    • Reedijk In, J.1
  • 12
    • 0037205912 scopus 로고    scopus 로고
    • A related pyridine bisdiphenyloxazoline type ligand, although highly enantioselective (up to 86% ee), has required reaction times of up to seventy five days. This also resulted in relatively low yields of the desired reaction products in some instances, see:
    • M. B. Andrus Z. Zhou J. Am. Chem. Soc. 2002 124 8806
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 8806
    • Andrus, M.B.1    Zhou, Z.2
  • 13
    • 0001423510 scopus 로고    scopus 로고
    • A pinene-derived bipyridyl ligand has been shown to be particularly effective for copper(i)-catalyzed asymmetric allylic oxidation reactions (reaction times of ca. 30 min and up to 75% ee), see:
    • G. Sekar A. DattaGupta V. K. Singh J. Org. Chem. 1998 63 2961
    • (1998) J. Org. Chem. , vol.63 , pp. 2961
    • Sekar, G.1    Dattagupta, A.2    Singh, V.K.3
  • 15
    • 0037603215 scopus 로고    scopus 로고
    • In addition to bisoxazolines, chiral nonracemic bicyclic proline derivatives, tridentate trisoxazolines ligands and a pinene-derived 1,10-phenanthroline ligand have also been found to perform well in copper(i)-catalyzed asymmetric allylic oxidation reactions, see:
    • A. V. Malkov D. Pernazza M. Bell M. Bella A. Massa F. Teplý P. Meghani P. Koovský J. Org. Chem. 2003 68 4727
    • (2003) J. Org. Chem. , vol.68 , pp. 4727
    • Malkov, A.V.1    Pernazza, D.2    Bell, M.3    Bella, M.4    Massa, A.5    Teplý, F.6    Meghani, P.7    Koovský, P.8
  • 19
    • 0025333283 scopus 로고
    • 4 See: R. Hayes T. W. Wallace Tetrahedron Lett. 1990 31 3355, This preparation of the former compound by catalytic means represents a marked improvement over previous routes which required multiple steps from carbohydrate-based starting materials
    • (1990) Tetrahedron Lett. , vol.31 , pp. 3355
    • Hayes, R.1    Wallace, T.W.2
  • 20
    • 33645688751 scopus 로고    scopus 로고
    • Note
    • For discussion and experimental procedures regarding the use of phenylhydrazine in the generation of copper(i) complexes from copper(ii) species, see: ref. ref. 10 and citations therein.
  • 21
    • 33645655645 scopus 로고    scopus 로고
    • Note
    • MINOR = 23.5 min]
  • 22
    • 33645669502 scopus 로고    scopus 로고
    • Note
    • A related mechanistic interpretation has been reported by Andrus and Zhou (ref. 9)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.