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Volumn 40, Issue 47, 1999, Pages 8205-8209

Carbon-carbon bond formation via the Mitsunobu reaction on solid supports

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKYL GROUP; AMIDE; PHOSPHINE DERIVATIVE; POLYMER;

EID: 0033584987     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01705-0     Document Type: Article
Times cited : (10)

References (18)
  • 13
    • 0009479858 scopus 로고    scopus 로고
    • note
    • The syntheses were performed in a parallel array on a robotic liquid handler synthesizer (SOLARIS™). The additions, aspirations, and washings were performed using a robotic arm possessing four alternate aspirating and coaxial tips. The 4-(2′,4′-dimethoxyphenylfluorenylmethoxycarbonylaminomethyl)phenoxy polystyrene, 'Rink Amide resin', loaded at 0.6 mmol Fmoc-amine/gm was placed in a round bottomed flask and was subjected to Fmoc cleavage with 20% piperidine in DMF for 10 min. The resin was subjected to a series of washings (3x5 mL) with DMF, MeOH, and DCM. Subsequently, the next step was coupling of the HMBA to the resin using 3 equivalents of DIC, HOBt, and HMBA in DMA for 4 h. At this stage, the solvent was drained and each flask was subjected to standard washing cycles. The next step was the Mitsunobu C-C alkylation using fivefold excess of tributylphosphine, N,N,N′,N′ -tetramethylazodicarboxamide, and the active methylene compounds was conducted in dry THF at room temperature. After shaking the mixture for 12 h at room temperature, the reagents were drained and the resin was subjected to the washing cycles. Cleavage of products from the resin was performed with 20% TFA in DCM over 45 min at rt gave the desired compounds.
  • 14
    • 0009514196 scopus 로고    scopus 로고
    • Structure of dimeric ester and the resultant Mitsunobu product product: (equation presented)
    • Structure of dimeric ester and the resultant Mitsunobu product product: (equation presented)
  • 17
    • 0031317101 scopus 로고    scopus 로고
    • Hodge, P. Chem. Rev. 1997, 26, 417-424.
    • (1997) Chem. Rev. , vol.26 , pp. 417-424
    • Hodge, P.1
  • 18
    • 0003008165 scopus 로고    scopus 로고
    • and references cited therein
    • Yan, B.; Sun, Q. J. Org. Chem. 1998, 63, 55-58 and references cited therein.
    • (1998) J. Org. Chem. , vol.63 , pp. 55-58
    • Yan, B.1    Sun, Q.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.