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Volumn 3, Issue 15, 2005, Pages 2805-2816

Evaluation of a new linker system cleaved using samarium(II) iodide. Application in the solid phase synthesis of carbonyl compounds

Author keywords

[No Author keywords available]

Indexed keywords

CARBON CARBON COMPOSITES; CHROMATOGRAPHY; ELECTRON TRANSITIONS; HALOGEN COMPOUNDS; KETONES; QUENCHING; SUBSTRATES; SYNTHESIS (CHEMICAL); TRACE ANALYSIS;

EID: 23844511244     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b506294b     Document Type: Article
Times cited : (27)

References (73)
  • 6
    • 0033574590 scopus 로고    scopus 로고
    • For reviews on linkers and cleavage strategies for solid phase organic synthesis, see: (a) I. W. James, Tetrahedron, 1999, 55, 4855;
    • (1999) Tetrahedron , vol.55 , pp. 4855
    • James, I.W.1
  • 14
    • 2142715741 scopus 로고    scopus 로고
    • For recent reviews on the use of samarium(II) iodide in organic synthesis: (a) G. A. Molander and C. R. Harris, Chem. Rev., 1996, 96, 307;
    • (1996) Chem. Rev. , vol.96 , pp. 307
    • Molander, G.A.1    Harris, C.R.2
  • 41
    • 0031562032 scopus 로고    scopus 로고
    • Janda has reported a single, sulfone example of this linkage as a member of a different, general class of sulfone linker. Cleavage of the linker is achieved using sodium/mercury amalgam: X. Zhao, K. W. Jung and K. D. Janda, Tetrahedron Lett., 1997, 38, 977.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 977
    • Zhao, X.1    Jung, K.W.2    Janda, K.D.3
  • 46
    • 0032537215 scopus 로고    scopus 로고
    • (b) X. Du and R. W. Armstrong, Tetrahedron Lett., 1998, 39, 2281. Further applications of the reagent on solid phase have since been reported.;
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2281
    • Du, X.1    Armstrong, R.W.2
  • 57
    • 0026059141 scopus 로고
    • The fragmentation of cyclopropyl ketones on treatment with samarium(II) iodide has been exploited previously in both synthetic and mechanistic contexts. (a) R. A. Batey and W. B. Motherwell, Tetrahedron Lett., 1991, 43, 6211;
    • (1991) Tetrahedron Lett. , vol.43 , pp. 6211
    • Batey, R.A.1    Motherwell, W.B.2
  • 63
    • 33645271369 scopus 로고    scopus 로고
    • note
    • Molander and Inanaga have invoked the direct reduction of the α-substituent in the case of α-bromo esters (ref. 5a) and α,β-epoxy esters (ref. 5c), respectively.
  • 70
    • 33645273922 scopus 로고    scopus 로고
    • note
    • Adduct 26 could conceivably be formed by radical addition to methylacrylate. The analogous reaction using an electronically matched radical acceptor, ethyl vinyl ether gave no addition products suggesting 26 is formed by an anionic process.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.