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Fluoride-catalyzed Michael addition of nitrotoluenes to activated α, β-unsaturated esters

✍ Scribed by Wen-Sen Li; John Thottathil; Michael Murphy


Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
217 KB
Volume
35
Category
Article
ISSN
0040-4039

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✦ Synopsis


We have found that in the presence of fluoride ion, nitrotoluenes of type 1 undergo Michael addition to activated a, p-unsaturated esters of type 2 in good to excellent yield (Scheme 1). The generality and limitation of this reaction and its application to the chiral synthesis of benzazepine 4 are described.


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A stereoselective michael addition of α-
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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.