The selective O-acylation of enolates providing simple entry to O-enesters

In the presence of catalytic amts. of a fluoride source, O-trimethylsilyl enethers undergo condensation with acyl fluorides to afford O-enesters with high yields. The intermediates and final products are pure (Z) isomers if only one double bond is in conjugation with the oxygen atom whereas (E) isomers prevail if silyl dienethers or trienethers and O-dienesters or O-triensesters are formed. [on SciFinder (R)]


Publié dans:
Tetrahedron, 51, 20, 5799-806
Année
1995
Mots-clefs:
Note:
CAN 123:255835
21-2
General Organic Chemistry
Inst. Chim. Org.,Univ. Batiment Chim.,Lausanne-Dorigny,Switz.
Journal
0040-4020
written in English.
16984-48-8 (Fluoride) Role: CAT (Catalyst use), USES (Uses) (selective O-acylation of enolates providing simple entry to O-enesters); 75-36-5 (Acetyl chloride); 79-03-8 (Propanoyl chloride); 93-97-0; 98-88-4 (Benzoyl chloride); 108-24-7 (Acetic anhydride); 112-67-4 (Hexadecanoyl chloride); 123-62-6; 334-19-0 (Heptanoyl fluoride); 430-71-7 (Propionyl fluoride); 430-92-2 (Isobutyryl fluoride); 455-32-3 (Benzoyl fluoride); 532-24-1 (Tropinone); 557-99-3 (Acetyl fluoride); 626-27-7; 1598-93-2 (10-Undecenoyl fluoride); 2528-61-2 (Heptanoyl chloride); 3872-13-7 (Hexadecanoyl fluoride); 6213-94-1; 6651-36-1; 19980-22-4; 36045-78-0; 50300-19-1; 52186-50-2; 52387-36-7 (6-Chlorohexanal); 56219-03-5; 63383-46-0; 65405-70-1 (trans-4-Decenal); 71504-21-7; 73912-36-4; 146271-53-6; 146271-54-7; 169216-34-6; 169216-35-7; 169216-48-2 Role: RCT (Reactant), RACT (Reactant or reagent) (selective O-acylation of enolates providing simple entry to O-enesters); 42082-93-9P; 121846-51-3P; 169216-37-9P; 169216-38-0P; 169216-39-1P; 169216-40-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (selective O-acylation of enolates providing simple entry to O-enesters); 115-22-0P; 693-38-9P (Vinyl palmitate); 2424-36-4P; 19980-23-5P; 57576-60-0P; 74322-79-5P; 84262-84-0P; 93675-37-7P; 165614-45-9P; 165614-47-1P; 165614-50-6P; 165614-51-7P; 165614-52-8P; 165614-53-9P; 169216-41-5P; 169216-42-6P; 169216-43-7P; 169216-44-8P; 169216-45-9P; 169216-46-0P; 169216-47-1P Role: SPN (Synthetic preparation), PREP (Preparation) (selective O-acylation of enolates providing simple entry to O-enesters)
Laboratoires:




 Notice créée le 2006-03-03, modifiée le 2018-01-27


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