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Volumn 46, Issue 14, 2005, Pages 2369-2371

Synthesis of 2-substituted piperazines via direct α-lithiation

Author keywords

DMG; DoM; Piperazines; Transmetallation; Lithiation

Indexed keywords

PIPERAZINE DERIVATIVE;

EID: 17744400080     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.085     Document Type: Article
Times cited : (100)

References (30)
  • 19
    • 85030804812 scopus 로고    scopus 로고
    • note
    • 2Si: 349.2311. Found: 349.2297
  • 28
    • 85030805245 scopus 로고    scopus 로고
    • note
    • 2: 316.2151. Found: 316.2161
  • 29
    • 0001692739 scopus 로고    scopus 로고
    • 2:281.2229.Found:281.2231. ToobtainfurtherproofoftherelativestereochemistrytheBocgroupwasremovedto liberatethesecondaryamine,nowamenableforasymmetricfunctionalisation. AttemptstoacylatetheresultingaminewithMosher'sacidchloridegroupfailedand gaveseveralsideproducts.Mostprobably,duetosterichindrancecausedbythe2, 6-allylgroups,sidereactionsatthe4-amineoccurred.(See:
    • 2: 281.2229. Found: 281.2231. To obtain further proof of the relative stereochemistry the Boc group was removed to liberate the secondary amine, now amenable for asymmetric functionalisation. Attempts to acylate the resulting amine with Mosher's acid chloride group failed and gave several side products. Most probably, due to steric hindrance caused by the 2,6-allyl groups, side reactions at the 4-amine occurred. (See: T.R. Hoye, and M.K. Renner J. Org. Chem. 61 1996 2056 2064). Addition of Pirkle's amine (up to 1.5 equiv) only gave a shift of the peaks. The observation that no doubling of the peaks occurred points at an achiral compound thus supporting the previous coupling constant based 2,6-cis stereochemistry assignment
    • (1996) J. Org. Chem. , vol.61 , pp. 2056-2064
    • Hoye, T.R.1    Renner, M.K.2
  • 30


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.