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Volumn 11, Issue 18, 2009, Pages 4076-4079

Palladium-catalyzed decarboxylative rearrangements of allyl 2,2,2-trifluoroethyl malonates: direct access to homoallylic esters

Author keywords

[No Author keywords available]

Indexed keywords

MALONIC ACID DERIVATIVE; METHYLMALONIC ACID; PALLADIUM;

EID: 70349134351     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901518g     Document Type: Article
Times cited : (17)

References (30)
  • 18
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    • For total synthesis of (-)-5'-homoaristeromycin, see: (a)
    • For total synthesis of (-)-5'-homoaristeromycin, see: (a) Roberts, S. M.; Jones, M. F. J. Chem. Soc., Perkin Trans. I 1988, 2927.
    • (1988) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 2927
    • Roberts, S.M.1    Jones, M.F.2
  • 20
    • 58149291860 scopus 로고    scopus 로고
    • For N-O bond reductions of cycloadducts, see
    • For N-O bond reductions of cycloadducts, see: Cesario, C.; Tardibono, L.; Miller, M. J. J. Org. Chem. 2009, 74, 448.
    • (2009) J. Org. Chem. , vol.74 , pp. 448
    • Cesario, C.1    Tardibono, L.2    Miller, M.J.3
  • 23
    • 70349153566 scopus 로고    scopus 로고
    • For a detailed table of reaction conditions, see Supporting Information.
    • For a detailed table of reaction conditions, see Supporting Information.
  • 24
    • 70349152333 scopus 로고    scopus 로고
    • The reaction is performed under anhydrous conditions in a sealed tube. High yields (76%) were observed on a 1.5 mmol scale. Decreased yields (61%) were observed on a 6 mmol scale.
    • The reaction is performed under anhydrous conditions in a sealed tube. High yields (76%) were observed on a 1.5 mmol scale. Decreased yields (61%) were observed on a 6 mmol scale.
  • 25
    • 70349102187 scopus 로고    scopus 로고
    • 1H NMR and showed complete consumption of the allyl 2,2,2-trifluoroethyl malonate and the formation of a single product with complete diastereo- and regiocontrol.
    • 1H NMR and showed complete consumption of the allyl 2,2,2-trifluoroethyl malonate and the formation of a single product with complete diastereo- and regiocontrol.
  • 26
    • 0001364588 scopus 로고    scopus 로고
    • For a brief discussion of coupling constants of 1,4-disubstituted cyclopentenes, see
    • For a brief discussion of coupling constants of 1,4-disubstituted cyclopentenes, see: Mulvihill, M. J.; Surman, M. D.; Miller, M. J. J. Org. Chem. 1998, 63, 4874.
    • (1998) J. Org. Chem. , vol.63 , pp. 4874
    • Mulvihill, M.J.1    Surman, M.D.2    Miller, M.J.3
  • 28
    • 13244296835 scopus 로고    scopus 로고
    • For mechanistic discussions of the decarboxylative Claisen rearrangement, see: (a)
    • For mechanistic discussions of the decarboxylative Claisen rearrangement, see: (a) Bourgeois, D.; Craig, D.; King, N. P.; Mountford, D. M. Angew. Chem., Int. Ed. 2005, 44, 618.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 618
    • Bourgeois, D.1    Craig, D.2    King, N.P.3    Mountford, D.M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.