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Volumn 45, Issue 8, 2004, Pages 1797-1801

Synthesis of C1-alkyl- and acylglycals from glycals using a B-alkyl Suzuki-Miyaura cross coupling approach

Author keywords

B Alkyl Suzuki Miyaura; C glycoside; Cross coupling; Glycal

Indexed keywords

ALKYL GROUP; BORANE DERIVATIVE; GLYCAL; REAGENT; UNCLASSIFIED DRUG;

EID: 0842283394     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.006     Document Type: Article
Times cited : (57)

References (59)
  • 9
    • 0002059047 scopus 로고    scopus 로고
    • For alternative approaches from non-glycal starting materials, see:
    • For alternative approaches from non-glycal starting materials, see: Gómez A.M., Casillas M., Valverde S., López J.C. Chem. Commun. 1996;2357-2358.
    • (1996) Chem. Commun. , pp. 2357-2358
    • Gómez, A.M.1    Casillas, M.2    Valverde, S.3    López, J.C.4
  • 28
    • 85030900384 scopus 로고    scopus 로고
    • note
    • 3SnCl (Scheme 2).
  • 29
    • 0001642353 scopus 로고
    • In contrast, successful alkylation of a dihydropyran lacking a C3-oxygen substituent has been reported using alkyl iodide
    • In contrast, successful alkylation of a dihydropyran lacking a C3-oxygen substituent has been reported using alkyl iodide 2 : Amouroux R. Heterocycles. 22:1984;1489-1492.
    • (1984) Heterocycles , vol.22 , pp. 1489-1492
    • Amouroux, R.1
  • 40
    • 85030898274 scopus 로고    scopus 로고
    • note
    • Attempts to access the C1-iodoglycals directly from the C1-lithioglycals were unsuccessful.
  • 49
    • 85030906417 scopus 로고    scopus 로고
    • note
    • The dppf mono(phosphine oxide) is presumably formed initally during reduction of Pd(II) to the active Pd(0) catalyst (Ref. 32).
  • 52
    • 85030897334 scopus 로고    scopus 로고
    • note
    • 2) yielded C1-alkylglycal 3a as a colorless oil (95.5 mg, 88%).
  • 53
    • 85030900187 scopus 로고    scopus 로고
    • note
    • Attempted couplings with exo-glycal-derived alkyl boranes yielded mixtures of cyclic and ring-opened C1-substituents under our conditions (cf. Ref. [26a]).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.