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Volumn , Issue 7, 2007, Pages 1115-1117

Samarium metal promoted facile C-acetylation of Baylis-Hillman adducts in the presence of iron(III) chloride and iodine

Author keywords

Baylis Hillman adduct; C acetylation; Metallic samarium; Stereoselective

Indexed keywords

FERROUS CHLORIDE; IODINE; SAMARIUM;

ACETYLATION; ARTICLE; BAYLIS HILLMAN REACTION; REDUCTION; STEREOCHEMISTRY;

EID: 34248195433 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-973901 Document Type: Article

Times cited : (15)

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- General Procedure for C-Acetylation of Baylis-Hillman Adducts To a stirred solution of 6 mmol Sm powder (0.9 g) and 6 mmol Ac2O (0.6 g) in 15 mL THF, 5 mol% FeCl3, 4 mol% I2 and 1 mmol Baylis-Hillman adduct 1 were added. The resulting mixture was then allowed to reflux in the air. Until completion of the reaction, 3 mL HCl (1 M) was then added to quench the reaction and the mixture was successively exacted with CH2Cl2 (3 x 20 mL, The organic phase was washed with 15 mL sat. brine, dried over anhyd Na2SO4, and filtered. The solvent was removed under reduced pressure to give the crude products, which were purified by column chromatography using EtOAc and PE (1:10) as eluent. Selected spectroscopic data for compounds 2 follow. Compound 2a (R, Ph, 1H NMR (500 MHz, CDCl3, δ, 7.93 (s, 1 H, 7.37-7.27 (m, 5 H, 3.80 (s, 3 H, 3.62 (s, 2 H, 2.25 s, 3 H
- -1.

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