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Volumn 45, Issue 51, 2004, Pages 9447-9450

Asymmetric allylic oxidation of bridged-bicyclic alkenes using a copper-catalysed symmetrising-desymmetrising Kharasch-Sosnovsky reaction

Author keywords

Alkene; Catalytic; Enantioselective; Oxidation

Indexed keywords

ALKENE DERIVATIVE; BICYCLO COMPOUND; BRIDGED COMPOUND; COPPER;

EID: 8844233468     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.093     Document Type: Article
Times cited : (25)

References (40)
  • 1
    • 0035476406 scopus 로고    scopus 로고
    • For recent reviews concerning asymmetric copper-catalysed allylic oxidation of alkenes with peresters, see: J. Eames, and M. Watkinson Angew. Chem., Int. Ed. Engl. 40 2001 3567 3571
    • (2001) Angew. Chem., Int. Ed. Engl. , vol.40 , pp. 3567-3571
    • Eames, J.1    Watkinson, M.2
  • 3
    • 0000205884 scopus 로고
    • For early examples of asymmetric copper-catalysed allylic oxidation reactions, see: D.B. Denney, R. Napier, and A. Cammarata J. Org. Chem. 30 1965 3151 3153
    • (1965) J. Org. Chem. , vol.30 , pp. 3151-3153
    • Denney, D.B.1    Napier, R.2    Cammarata, A.3
  • 30
    • 8844276095 scopus 로고    scopus 로고
    • note
    • The intermediates 7d and 12b were crystalline solids and their structures were confirmed by X-ray crystallography. Crystallographic data (excluding structure factors) for the compounds 7d and 12b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 250614 (7d) and CCDC 250615 (12b). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, United Kingdom [fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ]
  • 34
    • 0000985957 scopus 로고
    • The relative configuration of the allylic oxidation product 16 was established by ester cleavage and comparison of NMR data for the resulting alcohol with literature data for exo- and endo-bicyclo[3.2.1]oct-3-en-2-ol: J.B. Stothers, and C.T. Tan Can. J. Chem. 55 1977 841 848
    • (1977) Can. J. Chem. , vol.55 , pp. 841-848
    • Stothers, J.B.1    Tan, C.T.2
  • 37
    • 0033612274 scopus 로고    scopus 로고
    • The alcohol (+)-18 has also been converted into (+)-bicyclo[3.2.1]oct-3- en-2-one and this ketone has been used to prepare natural products of known absolute configuration: H. Nagata, T. Taniguchi, M. Kawamura, and K. Ogasawara Tetrahedron Lett. 40 1999 4207 4210
    • (1999) Tetrahedron Lett. , vol.40 , pp. 4207-4210
    • Nagata, H.1    Taniguchi, T.2    Kawamura, M.3    Ogasawara, K.4
  • 38
    • 0029078472 scopus 로고
    • For some recent reviews concerning microwave assisted organic reactions, see: S. Caddick Tetrahedron 51 1995 10403 10432
    • (1995) Tetrahedron , vol.51 , pp. 10403-10432
    • Caddick, S.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.