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Volumn 52, Issue 14, 2011, Pages 1549-1552

A stereoselective approach to 6-alkylated piperidinone & 2-piperidine via three-component vinylogous Mannich reactions (VMR) and a concise synthesis of (S)-anabasine

Author keywords

Anabasine; Asymmetric synthesis; Piperidine; Piperidinone; Vinylogous Mannich reaction

Indexed keywords

ANABASINE; PIPERIDINE; PIPERIDONE DERIVATIVE; SILANE DERIVATIVE; SILYL KETENE ACETAL; UNCLASSIFIED DRUG;

EID: 79952362789     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.01.090     Document Type: Article
Times cited : (21)

References (38)
  • 17
    • 0000279109 scopus 로고
    • To our knowledge, only few references described synthesizing piperidone compounds through the vinylogous Mannich reactions by acyclic siyl enolates: S.M. Brandstadter, and I. Ojima Tetrahedron Lett. 28 1987 613
    • (1987) Tetrahedron Lett. , vol.28 , pp. 613
    • Brandstadter, S.M.1    Ojima, I.2
  • 20
    • 53249126965 scopus 로고    scopus 로고
    • Schneider et al reported the asymmetric vinylogous Mannich reaction of vinylketen silyl acetal catalyzed by chiral Bronsted acid. To our knowledge, it is the only example of asymmetric VMR using similar acylic dienolate in literature. M. Sickert, and C. Schneider Angew. Chem., Int. Ed. 47 2008 3631
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 3631
    • Sickert, M.1    Schneider, C.2
  • 22
    • 79952360358 scopus 로고    scopus 로고
    • note
    • 13C-NMR (100 MHz, MeOD, 25 °C): δ = 24.55, 26.51, 26.55, 26.68, 29.01, 29.66, 33.69, 41.27, 51.47, 58.66, 122.58, 123.05, 123.69, 125.31, 125.67, 125.73, 127.19, 129.02, 131.42, 134.02, 141.39, 147.53, 166.88. LC-MS: 100% (purity), m/e: 366 (M+1). HRMS: Calcd. for C24H32NO2 (M+H): 366.24330. Found: 366.24305.
  • 23
    • 79952361686 scopus 로고    scopus 로고
    • note
    • Very low or no stereoselectivities were observed when non-steric hinder aldehydes were employed and diastereomeric mixtures of adducts were difficult to be separated by conventional approaches.
  • 24
    • 79952362839 scopus 로고    scopus 로고
    • note
    • In the case of 4d, hydrogenation led to the decomposition of the compound.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.