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Volumn , Issue 19, 2005, Pages 3389-3397

Using a temporary silicon connection in a highly stereoselective synthesis of a new class of cyclic allenylsilanes

Author keywords

Cyclisations; Intramolecular allenylation; Lewis acids; Stereoselective synthesis; Temporary Silicon Connection

Indexed keywords

ISOMERS; SCAVENGING; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 29044439317     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918465     Document Type: Article
Times cited : (12)

References (40)
  • 1
    • 0003157467 scopus 로고    scopus 로고
    • Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Chap. 10
    • For general reviews on the use of the 'Temporary Connection' in synthesis: (a) Cox, L. R.; Ley, S. V. In Templated Organic Synthesis; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 2000, Chap. 10, 275-375.
    • (2000) Templated Organic Synthesis , pp. 275-375
    • Cox, L.R.1    Ley, S.V.2
  • 6
    • 29044432919 scopus 로고    scopus 로고
    • note
    • Tri-tert-butylpyrimidine (TTBP) and 2,6-di-tert-butyl-4-methylpyridine (2,6-DTBMP) were equally effective in this role.
  • 8
    • 29044445408 scopus 로고    scopus 로고
    • Ph.D. Thesis; University of Birmingham: Birmingham
    • Beignet, J. Ph.D. Thesis; University of Birmingham: Birmingham, 2004.
    • (2004)
    • Beignet, J.1
  • 15
    • 17444413420 scopus 로고    scopus 로고
    • For some recent examples of allenylsilanes in synthesis: (a) Pacheco, M. C.; Gouverneur, V. Org. Lett. 2005, 7, 1267.
    • (2005) Org. Lett. , vol.7 , pp. 1267
    • Pacheco, M.C.1    Gouverneur, V.2
  • 20
    • 33645417371 scopus 로고    scopus 로고
    • Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, Chap. 4.4.32; and references cited therein
    • (f) See also: Pornet, J. In Science of Synthesis; Fleming, I., Ed.; Georg Thieme Verlag: Stuttgart, 2002, Chap. 4.4.32, 669-683; and references cited therein.
    • (2002) Science of Synthesis , pp. 669-683
    • Pornet, J.1
  • 21
    • 29044438372 scopus 로고    scopus 로고
    • note
    • The silyl tether is part of a vinylsilane in this intermediate and will be less effective in stabilising the β-vinyl carbocation on geometric grounds.
  • 32
    • 29044442781 scopus 로고    scopus 로고
    • note
    • Propargyltrimethylsilane is commercially available although expensive and invariably contaminated with varying amounts of allenyltrimethylsilane. We find it more convenient to prepare the reagent ourselves.
  • 34
    • 33845281940 scopus 로고
    • The β-hydroxy esters were prepared uneventfully by a Reformatski reaction between ethyl bromoacetate and the corresponding aldehyde: Picotin, G.; Miginiac, P. J. Org. Chem. 1987, 52, 4796.
    • (1987) J. Org. Chem. , vol.52 , pp. 4796
    • Picotin, G.1    Miginiac, P.2
  • 37
    • 0000557234 scopus 로고
    • 2,6-Di-tert-butylpyridine bound through the 4-position to a polystyrene support (1% divinylbenzene) is available from Aldrich or Fluka: Wright, M. E.; Pulley, S. R. J. Org. Chem. 1987, 52, 1623.
    • (1987) Org. Chem. , vol.52 , pp. 1623
    • Wright, M.E.1    Pulley, S.R.J.2
  • 38
    • 85005706466 scopus 로고
    • and references cited therein
    • Allylsilanes are particularly susceptible to decomposition in the presence of Broønsted acids: Chan, T. H.; Fleming, I. Synthesis 1979, 761; and references cited therein.
    • (1979) Synthesis , pp. 761
    • Chan, T.H.1    Fleming, I.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.