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Volumn 39, Issue 29, 1998, Pages 5181-5184

Expeditious formal synthesis of (±)-epibatidine using diastereoselective bromohydroxylation of aminocyclohexene derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ANTINOCICEPTIVE AGENT; BROMINE DERIVATIVE; EPIBATIDINE; OXAZOLIDINONE DERIVATIVE;

EID: 0032537715     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01017-X     Document Type: Article
Times cited : (62)

References (32)
  • 3
    • 84987014178 scopus 로고
    • For rewiews : see : (c) Dehmlow, E. V. J. Prakt. Chem. 1995, 337, 167-174.
    • (1995) J. Prakt. Chem. , vol.337 , pp. 167-174
    • Dehmlow, E.V.1
  • 15
    • 0001071070 scopus 로고
    • 4. In our hands, bromohydroxylation of cyclohexadiene was accomplished in 47% yield following the Dalton's procedure : Dalton, D. R.; Dutta, V. P.; Jones, D. C. J. Am. Chem. Soc. 1968, 90, 5498-5501.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 5498-5501
    • Dalton, D.R.1    Dutta, V.P.2    Jones, D.C.3
  • 16
    • 0027442712 scopus 로고
    • 5. Dibromination of the double bond of a functionalized cyclohexene has been reported by Corey's group and proved to be totally diastereoselective : Corey, E. J.; Loh, T. -P.; AchyuthaRao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600-5602.
    • (1993) J. Org. Chem. , vol.58 , pp. 5600-5602
    • Corey, E.J.1    Loh, T.-P.2    AchyuthaRao, S.3    Daley, D.C.4    Sarshar, S.5
  • 17
    • 0010414605 scopus 로고    scopus 로고
    • note
    • 6. Compounds 4a et 4b showing some instability, and could not be isolated separately by chromatography on silica gel. The product ratio was determined as 65/35 by NMR analysis but the major product could not be identified.
  • 18
    • 0010379824 scopus 로고    scopus 로고
    • note
    • +).
  • 27
    • 0010379825 scopus 로고    scopus 로고
    • note
    • +) ; 238/236.
  • 32
    • 0010379826 scopus 로고    scopus 로고
    • note
    • +) ; 157; 155.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.