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Volumn 13, Issue 1, 2009, Pages 84-90

New efficient asymmetric synthesis of taranabant, a CB1R inverse agonist for the treatment of obesity

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EID: 61449254504     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op800270e     Document Type: Article
Times cited : (58)

References (40)
  • 29
    • 0037049225 scopus 로고    scopus 로고
    • For Pd-catalyzed amination of enol triflates, see:(a) Willis, M. C.; Brace, G. N. Tetrahedron Lett. 2002, 43, 9085.
    • For Pd-catalyzed amination of enol triflates, see:(a) Willis, M. C.; Brace, G. N. Tetrahedron Lett. 2002, 43, 9085.
  • 32
    • 61449263156 scopus 로고    scopus 로고
    • The underlying factors controlling the enolization selectivity are not clear; however, it is felt that highly coordinating solvents (DMAC, DMF) could change the aggregation state of the enolate which in turn may contribute to selectivity. Additionally, potential coordination of the aryl nitrile group to the enolate metal is possible in the E-enolate (leading to 10a) but not in the Z-enolate (leading to 10b) which may also account for changes with metal and solvent.
    • The underlying factors controlling the enolization selectivity are not clear; however, it is felt that highly coordinating solvents (DMAC, DMF) could change the aggregation state of the enolate which in turn may contribute to selectivity. Additionally, potential coordination of the aryl nitrile group to the enolate metal is possible in the E-enolate (leading to 10a) but not in the Z-enolate (leading to 10b) which may also account for changes with metal and solvent.
  • 33
    • 61449166067 scopus 로고    scopus 로고
    • 2, MeCN) followed by quenching with ammonium hydroxide.
    • 2, MeCN) followed by quenching with ammonium hydroxide.
  • 34
    • 0038579438 scopus 로고    scopus 로고
    • For beneficial effects of tert-amyl alcohol in palladium-catalyzed processes, see: (a) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
    • For beneficial effects of tert-amyl alcohol in palladium-catalyzed processes, see: (a) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
  • 40
    • 61449119065 scopus 로고    scopus 로고
    • 31P NMR spectra.
    • 31P NMR spectra.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.