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Volumn 71, Issue 5, 2006, Pages 2071-2077

Stereoselective synthesis of new chiral N-tertiary tetrasubstituted β-enamino ester piperidines through an ammonia-catalyzed process

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVE FORMATION; ESTER PIPERIDINES; PIPERIDINE;

EID: 33644651112     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052490p     Document Type: Article
Times cited : (11)

References (38)
  • 18
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    • note
    • 3 was totally converted into 6a over 6 h.
  • 19
    • 33644643169 scopus 로고    scopus 로고
    • note
    • The obtention of 6a was also observed using deactivated silica gel which prevented any further purification.
  • 20
    • 33644655620 scopus 로고    scopus 로고
    • note
    • 3.
  • 21
    • 0000134173 scopus 로고
    • Trost B. M., Ed.; Pergamon Press: Oxford
    • Shiosaki, K. In Comprehensive Organic Chemistry; Trost B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2. pp 865-892.
    • (1991) Comprehensive Organic Chemistry , vol.2 , pp. 865-892
    • Shiosaki, K.1
  • 23
    • 33644646316 scopus 로고    scopus 로고
    • note
    • Among the different reaction conditions screened: (a) condensation without solvent at 110 °C;
  • 24
    • 33644647303 scopus 로고    scopus 로고
    • note
    • 3CN;
  • 25
    • 33644653526 scopus 로고    scopus 로고
    • note
    • 2 at 65 °C;
  • 26
    • 33644648692 scopus 로고    scopus 로고
    • note
    • 2.
  • 27
    • 33644654121 scopus 로고    scopus 로고
    • note
    • ω-Chloro and/or ω-amino enamino esters were obtained as side products depending on the reaction conditions.
  • 28
    • 33644654554 scopus 로고    scopus 로고
    • note
    • 2c no in situ cyclisation of intermediate 6a into compound 2a occurred during the deprotection step.
  • 30
    • 33644654262 scopus 로고    scopus 로고
    • note
    • Contrary to 2a, silica gel column chromatography of compounds 2b-d generates only a small amount of linear amines 6b-d.
  • 33
    • 33644662443 scopus 로고    scopus 로고
    • note
    • 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.