SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 11, 2007, Pages 1703-1706

3-vinyl-2,5-dihydrofuran derivatives via enyne metathesis

(4) Rodriguez Fernandez, M Mercedes a Vuong, Sophie a Renoux, Brigitte a Len, Christophe a

a UNIVERSITÉ DE POITIERS (France)

Author keywords

Carbohydrate; Cyclization; Enyne; Furan; Metathesis

Indexed keywords

3 VINYL 2,5 DIHYDROFURAN DERIVATIVE; ALKYNE DERIVATIVE; CARBENOID; CARBON; FURAN DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CATALYSIS; CATALYST; RACEMIZATION; RING CLOSING METATHESIS;

EID: 34447529369 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-984503 Document Type: Article

Times cited : (6)

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- 2 (12 mL) was then added and the mixture was stirred under ethylene at 20°C during 5 d. The volatiles were eliminated under reduced pressure and the residue was purified by flash chromatography (5% EtOAc in hexane) to give rac-cis-22 (100 mg, 25%) and rac-trans-22 (100 mg, 25%) in order effractions eluted.
- 2 (12 mL) was then added and the mixture was stirred under ethylene at 20°C during 5 d. The volatiles were eliminated under reduced pressure and the residue was purified by flash chromatography (5% EtOAc in hexane) to give rac-cis-22 (100 mg, 25%) and rac-trans-22 (100 mg, 25%) in order effractions eluted.

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- Selected physico-chemical data for compound cis-12: Rf, 0.50 (5% EtOAc-hexane, 1H NMR (300 MHz, CDCl3, δ, 7.71 (m, 4 H, Ph, 7.45 (m, 6 H, Ph, 6.48 (dd, 1 H, J, 12, 18 Hz, CH, 6.18 (s, 1 H, H3, 5.87 (s, 1 H, H5, 5.46 (d, 1 H, J, 18 Hz, CH, 5.23 (d, 1 H, J, 12 Hz, CH, 4.80 (m, 1 H, J, 1 Hz, H2, 3.68 (m, 4 H, OCH2CH3, CH2OSi, 1.23 (t, 3 H, J, 8 Hz, CH3, 1.06 (s, 9 H, 3 CH3) ppm. 13C NMR (75 MHz, CDCl3, δ, 138.9 (C4, 136.0 (Ph, 135.9 (Ph, 133.9 (C3, 133.8 (Ph, 130.4, CH, 128.1 (Ph, 118.0, CH2, 107.6 (C5, 85.7 (C2, 67.6 (CH 2OSi, 62.6 (OCH2, 27.2 (CH3 of t-Bu, 19.6(Cq of t-Bu, 15.8 (CH3) ppm. ESI-HRMS: m/z calcd [M, Na
- +]: 431.2018; found: 431.2034.

42
- 34447509922
- Selected physico-chemical data for compound trans-12: Rf, 0.20 (5% MeOH-CH2Cl2, 1H NMR (300 MHz, CDCl3, δ, 7.65 (m, 4 H, Ph, 7.38 (m, 6 H, Ph, 6.43 (m, 1 H, J, 12, 18Hz, CH, 5.98 (s, 1 H, H 3, 5.96 (d, 1 H, J, 4 Hz, H5, 5.43 (d, 1 H, J, 18, CH, 5.24 (d, 1 H, J, 12 Hz, CH, 4.90 (m, 1 H, H 2, 3.72 (m, 4 H, OCH2CH3, CH 2OSi, 1.26 (t, 3 H, J, 8 Hz, CH3, 1.04 (s, 9 H, 3 CH3) ppm. 13C NMR (75 MHz, CDCl3, δ, 138.8 (C4, 136.0 (Ph, 133.9 (Ph, 130.6 (C3, 130.0 (Ph, 129.0, CH, 128.1 (Ph, 118.0, CH2, 107.6 (C5, 85.6 (C2, 66.6 (CH2OSi, 62.1 (OCH2, 27.2 (CH3 of t-Bu, 19.6 (Cq of t-Bu, 15.8 CH 3, ESI-HRMS: m/z
- +]: 431.2018; found: 431.2025.

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