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Volumn 44, Issue 14, 2003, Pages 2939-2942

Development of a 9-borabicyclo[3.3.1]nonane-mediated solid-phase Suzuki coupling for the preparation of dihydrostilbene analogs

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BICYCLO COMPOUND; STILBENE DERIVATIVE;

EID: 0037474659     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00415-5     Document Type: Article
Times cited : (8)

References (26)
  • 18
    • 85031197469 scopus 로고    scopus 로고
    • 2/water, 30 min, rt)
    • 2/water, 30 min, rt).
  • 21
    • 85031197352 scopus 로고    scopus 로고
    • 16 was found to be 1.37 mmol/g or 105% of theoretical substitution. Just prior to the reaction with sulfonyl or carbonyl chloride, the resin was N-Fmoc-deprotected by treatment with 30% piperidine in DMF (30 min, rt), washed with DMF (5×), MeOH (3×), DCM (3×), and MeOH (3×), and dried in vacuo
    • 16 was found to be 1.37 mmol/g or 105% of theoretical substitution. Just prior to the reaction with sulfonyl or carbonyl chloride, the resin was N-Fmoc-deprotected by treatment with 30% piperidine in DMF (30 min, rt), washed with DMF (5×), MeOH (3×), DCM (3×), and MeOH (3×), and dried in vacuo.
  • 22
    • 85031196051 scopus 로고    scopus 로고
    • Conversion of 3 to 4 was achieved by treatment with 3 molar equiv. of the appropriate carbonyl or sulfonyl chloride, plus diisopropylethylamine (3 equiv.), in dichloromethane with mixing at rt overnight
    • Conversion of 3 to 4 was achieved by treatment with 3 molar equiv. of the appropriate carbonyl or sulfonyl chloride, plus diisopropylethylamine (3 equiv.), in dichloromethane with mixing at rt overnight.
  • 23
    • 85031210188 scopus 로고    scopus 로고
    • 2(dppf) (0.2 equiv.) in degassed DMF/water (9:1). The olefin/9-BBN reaction mixtures (7) were then added under argon, the reaction mixtures were capped, and the mixtures were mixed by orbital shaking at 50°C for 18 h. The mixtures were then cooled to rt, filtered, washed with DMF (7×), MeOH (5×), DCM (3×), MeOH (3×), and DCM (2×), and dried in vacuo. MicroKans were sorted, and then individually treated with 1:1:0.1 TFA/DCM/water at rt for 2 h, to release the products 1
    • 2(dppf) (0.2 equiv.) in degassed DMF/water (9:1). The olefin/9-BBN reaction mixtures (7) were then added under argon, the reaction mixtures were capped, and the mixtures were mixed by orbital shaking at 50°C for 18 h. The mixtures were then cooled to rt, filtered, washed with DMF (7×), MeOH (5×), DCM (3×), MeOH (3×), and DCM (2×), and dried in vacuo. MicroKans were sorted, and then individually treated with 1:1:0.1 TFA/DCM/water at rt for 2 h, to release the products 1.
  • 24
    • 85031208676 scopus 로고    scopus 로고
    • R 3.24 min.
    • 4S=415.2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.