The selective O-acylation of enolates providing simple entry to O-enesters
1995
Abstract
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)]
Details
Title
The selective O-acylation of enolates providing simple entry to O-enesters
Author(s)
Limat, Dominique ; Schlosser, Manfred
Published in
Tetrahedron
Volume
51
Issue
20
Pages
5799-806
Date
1995
ISSN
0040-4020
Keywords
Note
CAN 123:255835 21-2 General Organic Chemistry Inst. Chim. Org.,Univ. Batiment Chim.,Lausanne-Dorigny,Switz. Journal 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)
Laboratories
LSCO
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > SB Archives > LSCO - Laboratory of Organic Synthesis and Catalysis
Peer-reviewed publications
Work produced at EPFL
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Published
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date
2006-03-03