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-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.
## Abstract Enals react with various 1,3‐dicarbonyl compounds as redox‐activated Michael acceptors in the presence of TAZ as NHC precursor and a bisphenol derived quinone TBQ as the organic oxidant to produce dihydropyranones.