Aldol reaction of trimethylsilyl enolate with aldehyde catalyzed by pyridine N-oxide as a Lewis base catalyst

Synlett

Volumn , Issue 15, 2005, Pages 2388-2390

  Hagiwara, Hisahiro ^a   Inoguchi, Hideyuki ^a   Fukushima, Masakazu ^a   Hoshi, Takashi ^a   Suzuki, Toshio ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

Aldol reactions; Lewis base; Organomolecular catalysis; Pyridine N oxide; Trimethylsilyl ketene acetal

Indexed keywords

LEWIS BASE; PYRIDINE 1 OXIDE; TRIMETHYLSILYL DERIVATIVE; TRIMETHYLSILYL ENOLATE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; ROOM TEMPERATURE; STOICHIOMETRY;

EID: 25444451098     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872664     Document Type: Article

References (27)

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25. Typical experimental procedure: To a stirred solution of pyridine N-oxide (3.8 mg, 0.04 mmol) and LiCl (3.4 mmol, 0.08 mmol) in DMF (1.5 mL) were added benzaldehyde 2 (R = Ph) (42 μL, 0.4 mmol) and trimethylsilyl ketene acetal 1 (105 μL, 0.52 mmol) at r.t. under a nitrogen atmosphere. After stirring for 5 h, the reaction was quenched by the addition of 1 N aq HCl. The product was extracted with EtOAc twice. The combined organic layer was washed with water, brine, and evaporated to dryness. The residue was purified by medium-pressure LC (EtOAc-hexane, 1:2) to afford aldol product 3 (R = Ph) (92 mg, 81%) as a solid.
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