Reactions of cyclic nitrones with (E)-γ-hydroxy- and (E)-γ-alkoxy-α,β-unsaturated esters
✍ Scribed by P. de March; M. Figueredo; J. Font; M. Monsalvatje
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 422 KB
- Volume
- 114
- Category
- Article
- ISSN
- 0165-0513
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The 1,3-dipolar cycloaddition of cyclic nitrones to several "t-bromo ct,~unsaturated esters and lactones has been studied. All the reactions have shown high stereoselectivity, with a predominance of the endo or exo transition state for the trans or cis dipolarophiles, respectively.
e-Acetoxy-8,y-unsaturated nitriles react at room temperature with malonates and acetoacetates in the presence of palladium-phosphine complexes as a catalyst to give y-substituted a,8-unsaturated nitriles selectively. Also yacetoxy-a,8-unsaturated ester was attacked at y-position by malonate.