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Volumn , Issue 3, 2007, Pages 381-386

DMAP-organocatalyzed O-silyl-O-(or C-)-benzoyl interconversions by means of benzoyl fluoride

(6) Poisson, Thomas a Dalla, Vincent b Papamicaël, Cyril a Dupas, Georges a Marsais, Francis a Levacher, Vincent a

Author keywords

Acid fluorides; Alcohols; Benzoylation; Claisen condensation; Cyanohydrins; DMAP; Organocatalysis; Silyl ethers; Transprotection

Indexed keywords

4 DIMETHYLAMINOPYRIDINE; ACETONITRILE; BENZALDEHYDE; BENZOYL FLUORIDE; CYANOHYDRIN; FLUORIDE; KETONE DERIVATIVE; O BENZOYL CYANOHYDRINE DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CLAISEN CONDENSATION; ROOM TEMPERATURE;

EID: 33847415869 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-968028 Document Type: Article

Times cited : (33)

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- 2 (5 mL) was added TMSCl (115 mg, 1.05 mmol). The reaction was stirred at r.t. overnight. The solvent was removed under reduced pressure and the resultant residue was diluted with pentane (10 mL). Simple filtration through a short pad of Celite® provided silyl ether 1a in 95% yield which could be used in the silyl ether exchange reaction without further purification.
- 2 (5 mL) was added TMSCl (115 mg, 1.05 mmol). The reaction was stirred at r.t. overnight. The solvent was removed under reduced pressure and the resultant residue was diluted with pentane (10 mL). Simple filtration through a short pad of Celite® provided silyl ether 1a in 95% yield which could be used in the silyl ether exchange reaction without further purification.

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- General Procedure for the Transprotection of Silyl Ethers 1a-f, Silyl Enol Ethers 1m-o and Ketene Silyl Acetals 1p-r. To a solution of silylated alcohol 1f (268 mg, 1 mmol) and DMAP (12 mg, 0.1 mmol) in MeCN (2 mL) was added benzoyl fluoride (130 mg, 1.05 mmol, The resulting solution was stirred for 6 h at r.t, followed by addition of sat. aq NaHCO3 (4 mL, After phase separation, the aqueous phase was extracted with EtOAc (3 x 10 mL, The combined organic layers were washed with sat. aq NH4Cl (10 mL) and brine (10 mL, After drying (MgSO4) and evaporation of the organic solvents under vacuum, the resulting residue was chromatographed on silica gel (cyclohexane-EtOAc, 9:1) affording benzoate 2f in 62% yield. Selected Data for Benzoate 2f. 1H NMR (300 MHz, CDCl3, δ, 8.01 (s, 1 H, 7.97 (d, 2 H, J, 8.3 Hz, 7.46 (t, 1 H, J, 5.4 Hz, 7.27 (m, 3 H, 7.16 (m, 1 H, 6.85 m, 2 H, 5.2
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- -1. All other synthesized O-benzoyl cyanohydrins are in accordance with the literature data.

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34
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- For a recent contribution from our group in the chemistry of chiral DMAPs, see
- (b) For a recent contribution from our group in the chemistry of chiral DMAPs, see: Poisson, T.; Penhoat, M.; Papamicaël, C.; Dupas, G.; Dalla, V.; Marsais, F.; Levacher, V. Synlett 2005, 2285.
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