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Volumn , Issue 18, 2006, Pages 3069-3072

Diastereoselective heck arylation of spirolactams: An approach to spiroamine-based nicotinic ligands

Author keywords

Heck reaction; Lactams; Metathesis; Spirocycles; Stereoselectivity

Indexed keywords

AMINE; CARBONYL DERIVATIVE; LACTAM DERIVATIVE; NICOTINIC RECEPTOR; SPIROAMINE; SPIROLACTAM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33751303946     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951515     Document Type: Article
Times cited : (3)

References (29)
  • 3
    • 23944472732 scopus 로고    scopus 로고
    • (b) For an overview of the role of natural products as nicotinic ligands, see: Daly, J. W. Cell. Mol. Neurobiol. 2005, 25, 513.
    • (2005) Cell. Mol. Neurobiol. , vol.25 , pp. 513
    • Daly, J.W.1
  • 13
    • 0034127063 scopus 로고    scopus 로고
    • For reviews covering recent synthetic and mechanistic aspects of the Heck arylation reaction, see: (a) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 314
    • Amatore, C.1    Jutand, A.2
  • 17
    • 2942530606 scopus 로고    scopus 로고
    • A related sequence aimed at the spirocyclic core of spirolide marine toxins has been developed. See: Brimble, M. A.; Trzoss, M. Tetrahedron 2004, 60, 5613.
    • (2004) Tetrahedron , vol.60 , pp. 5613
    • Brimble, M.A.1    Trzoss, M.2
  • 18
    • 33751285457 scopus 로고    scopus 로고
    • note
    • 3), 39.9 (C-6), 50.3 (C-3), 125.3 and 125.0 (C-8, C-9), 175.0 (C-1).
  • 19
    • 33751263177 scopus 로고    scopus 로고
    • note
    • 11 (Heck arylation of 6a and 6c was not observed under these latter conditions). A number of other conditions, including use of Ag(I) as an activator, were also evaluated.
  • 22
    • 0000155224 scopus 로고
    • (c) For the application of an improved procedure for arylation of simple cycloalkenes, see: Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 2603
    • Larock, R.C.1    Gong, W.H.2    Baker, B.E.3
  • 24
    • 33751305375 scopus 로고    scopus 로고
    • note
    • 2O: C, 65.19; H, 6.20; N, 10.14. Found: C, 65.25; H, 6.11; N, 10.24.
  • 28
    • 33751292839 scopus 로고    scopus 로고
    • note
    • Alkene isomerisation under basic conditions (t-BuOK, DME, 60 °C) was observed but this could not be controlled and an inseparable 1:1 mixture of regioisomers was obtained.
  • 29
    • 33751271125 scopus 로고    scopus 로고
    • note
    • 3): δ = 19.2, 22.3, 29.0, 30.1, 35.4, 35.9, 40.5, 50.3, 122.5, 125.0, 126.7, 128.2, 134.7, 142.4, 175.8.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.