𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A highly stereoselective Michael reaction of simple ester enolates to α,β-unsaturated esters

✍ Scribed by Masahiko Yamaguchi; Michinori Tsukamoto; Shinya Tanaka; Ichiro Hirao

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
244 KB
Volume
25
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Under a proper reaction condition, simple ester enolates add to d,e-unsaturated esters highly stereoselectively to give erythro or threoglutarates.

Previously, we have shown that lithium enolates derived from simple monoesters react with fi,p-unsaturated esters to give glutarates in high yiela. 1) Under this reaction condition, however, the addition of ethyl propionate to P-monosubstituted unsaturates esters was not highly stereoselective, and a

📜 SIMILAR VOLUMES

A stereoselective michael addition of α-
A stereoselective michael addition of α-lithiated phosphonates to α,β-unsaturated esters
✍ Masahiko Yamaguchi; Yukiharu Tsukamoto; Akio Hayashi; Toru Minami 📂 Article 📅 1990 🏛 Elsevier Science 🌐 French ⚖ 123 KB

a-Lithiated phosphonates added to a&unsaturated t-butyl esters in 1,Gmanner giving anti-3,4-disubstituted-4-phosphorylbutanoates in high yields. /~~%~ylam%omethyl)phosphonates were prepared from dialkyl phosphite, dibenzylamine, and formaldehyde: See; R. Tyka, Tetrahedron Lett., 1970, 677.