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Tetrahedron Letters
Volumn 43, Issue 34, 2002, Pages 5973-5975
Low dilution procedures in solid-phase organic synthesis: Diels-Alder and Heck reactions
Author keywords

Diels Alder; Heck reaction; Low dilution; Polmyer support; Reagent concentration; Solid phase synthesis
Indexed keywords

ORGANIC COMPOUND; RESIN; SOLVENT;
EID: 0037136166     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01259-5     Document Type: Article
Times cited : (15)
References (18)
  • 6
  • 8
    • 33646449394 scopus 로고    scopus 로고
    • (1999) Chem. Rev. , vol.99 , pp. 1549-1581
  • 9
    • 0035128271 scopus 로고    scopus 로고
    • (2001) Chem. Rev. , vol.101 , pp. 137-202
  • 10
    • 0009906031 scopus 로고    scopus 로고
    • Reaction conditions for synthesis of polymer bound N-maleoyl-β-alanine 1: Wang resin (3.2 mmol) was swollen in THF (50 mL) and treated sequentially with N-maleoyl-β-alanine (11.8 mmol), triphenylphosphine (5.4 mmol) and diisopropylazodicarboxylate (6.1 mmol). The mixture was shaken at 20°C for 18 h, filtered, washed (3×30 mL THF, DMF, MeOH, DCM, MeOH) and dried in vacuo to give 1 as a colourless solid. Resin loading was determined by cleavage of 2×50 mg portions in 1:1 v/v DCM/TFA (0.53 mmol/g).
  • 13
    • 0009956420 scopus 로고    scopus 로고
    • Typical reaction conditions for the Diels-Alder reaction: Wang resin bound N-maleoyl-β-alanine (0.05 mmol) was treated with 2,3-dimethylbutadiene (0.1-0.25 mmol) and suspended in toluene (0-1 mL). The mixture was shaken at 20°C for 3 h, filtered, washed (3×1 mL toluene, DCM) and dried in vacuo. The resin was then suspended in DCM/TFA (1 mL, 1:1 v/v) and shaken at 20°C for 1 h. The product was then isolated by filtration and resin washing (3×1 mL DCM, 9:1 v/v DCM/MeOH).
  • 16
    • 0009957942 scopus 로고    scopus 로고
    • Reaction conditions for synthesis of polymer bound 3-iodobenzoic acid 4: Wang resin (3.2 mmol) was swollen in DCM (50 mL) and treated sequentially with DIEA (17.6 mmol) and 3-iodobenzoylchloride (17.6 mmol). The mixture was shaken at 20°C for 18 h, filtered, washed (3×30 mL DCM, DMF, DCM, MeOH) and dried in vacuo to give 4 as a sand coloured solid. Resin loading was determined by cleavage of 2×50 mg portions in 1:1 v/v DCM/TFA (1.06 mmol/g).
  • 18
    • 0009906032 scopus 로고    scopus 로고
    • 2O, DMF, DCM, MeOH). The resin was then suspended in DCM/TFA (1 mL, 1:1 v/v) and shaken at 20°C for 1 h. The product was isolated by filtration and resin washing (3×1 mL DCM, 9:1 v/v DCM/MeOH).

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