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Journal article

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)]

    Keywords: Stereochemistry (selective O-acylation of enolates providing simple entry to O-enesters); Esters Role: SPN (Synthetic preparation) ; PREP (Preparation) (selective O-acylation of enolates providing simple entry to O-enesters); Ethers Role: RCT (Reactant) ; selective acylation enolate; enol ester

    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)

    Reference

    Record created on 2006-03-03, modified on 2016-08-08

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