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Stereoselective synthesis of (E)- α, β -unsaturated acids from C,O,O-tri (trimethylsilyl) ketene acetal and aldehydes.

✍ Scribed by Moncef Bellassoued; Marcel Gaudemar

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
169 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

Aldehydes are converted into (E)-CI , fi -unsaturated carboxylic acids by means of C,O,O -tri(trimethylsilyl) ketene acetal and a catalytic amount of ZnBr2.

Several ways have been described to transform aldehydes into c1 , 6 -unsaturated esters.

However, the hydrolysis of the resultant esters to the corresponding ~1, 6 -unsaturated acids can

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Stereocontrolled synthesis of α,β-unsatu
Stereocontrolled synthesis of α,β-unsaturated carboxylic esters from O-methyl-C,O-bis(trimethylsilyl)ketene acetal and aliphatic aldehydes
✍ Isamu Matsuda; Yusuke lzumi 📂 Article 📅 1981 🏛 Elsevier Science 🌐 French ⚖ 241 KB

R\*,S\*) Selective aldol type reaction of O-methyl-C,O-bis(trimethylsilyl)ketene acetal (,j.) with aldehydes and stereoselective formation of c,B-unsaturated carboxylic esters are attained by the combination of 2-A and Lewis acids. One of the most versatile methods to E selective synthesis of a,$-un