SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 11, 2009, Pages 1733-1736

Phosphine-catalysed cyclisation of β-hydroxy-α,α- difluoroynones

(3) Schuler, Marie a Monney, Angèle a Gouverneur, Véronique a

a UNIVERSITY OF OXFORD (United Kingdom)

Author keywords

Catalysis; Fluorine; Furanone; Phosphine

Indexed keywords

BENZYLIDENE DERIVATIVE; CARBONYL DERIVATIVE; FLUORINE DERIVATIVE; FURANONE DERIVATIVE; PHOSPHINE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS; VALIDATION PROCESS;

EID: 67650094917 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217366 Document Type: Article

Times cited : (9)

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- General Procedure for Cyclisation of 1c To a solution of 1c (200 mg, 0.64 mmol, 1 equiv) in anhydrous toluene (64 mL) was added under argon AcOH (15 μL, 0.255 mmol, 40 mol, followed by dppp (26.3 mg, 0.064 mmol, 10 mol, The reaction mixture was stirred at 60 °C for 4 h. The crude mixture was concentrated in vacuo at r.t, and the resulting solution was directly purified by column chromatography on silica gel (hexane-Et2O, 80:20) to give the product as a yellow oil (120 mg, 0.38 mmol) in a 60% yield, Z)-2-Benzylidene-4,4-difluoro-5-(2-phenylethyl, dihydrofuran-3 (2H)-one (2c) Rf, 0.68 (hexane-EtOAc, 80:20, 1H NMR (400 MHz, CDCl3, δ, 2.25 (q, J, 7.3 Hz, 2 H, CH2CH, 2.91-3.04 (m, 2 H, CH2Ph, 4.44-4.55 (m, 1 H, CF2CH, 6.65 (s, 1 H, C=CHPh, 7.25-7.46 (m, 8 H, 8 × ArH, 7.79 br d, J, 6.8 Hz, 2 H, 2
- +: 315.1197; found: 315.1209.

39
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- Procedure for the Synthesis of 6c To a stirred solution of 5c (47.6 mg, 0.11 mmol, 1 equiv) in MeCN-CCl4-H2O (1.5:1:1, 1 mL) were added NaIO4 (141 mg, 0.66 mmol, 6 equiv) and RuCl3·H2O (0.9 mg, 4.4 μmol, 4 mol, After 30 min, the reaction mixture was quenched by addition of H2O, and it was extracted three times with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification by column chromatography on silica gel (hexane-Et2O, 95:5 to 90:10) gave the product as a white solid (26.5 mg, 74 μmol) in a 68% yield. Rf, 0.23 (hexane-Et2O, 95:5, 1H NMR (400 MHz, CDCl3, δ, 0.14 and 0.17 (2 × s, 6 H, 0.92 (s, 9 H, 2.05-2.15 (m, 2 H, 2.70-2.91 (m, 2 H, 4.25-4.36 (m, 1 H, 4.48 (dd, J, 14.8, 9.4 Hz, 1 H, 7.16-7.22 (m, 3 H, 7.25-7.32 m, 2
- 4]+.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.