Enantioselective Ruthenium-Catalyzed 1,3-Dipolar Cycloadditions between C-Carboalkoxy Ketonitrones and Methacrolein: Solvent Effect on Reaction Selectivity and Its Rationale.

In the presence of a nonracemic stilbenediol bis(phosphite) ruthenium complex, nitrones derived from ketoesters underwent diastereoselective and enantioselective 1,3-dipolar cycloaddn. reactions with methacrolein to give formylisoxazolidinecarboxylates; using Me tert-Bu ether or toluene as the solvent or using N-benzyl or N-Me nitrones yielded the endo- and exo-cycloadducts as the major diastereomers, resp. The solvent effect was rationalized based on interactions between the methacrolein-Ru complex and its hexafluoroantimonate counteranion found using computational methods.

Références

Titre
Enantioselective Ruthenium-Catalyzed 1,3-Dipolar Cycloadditions between C-Carboalkoxy Ketonitrones and Methacrolein: Solvent Effect on Reaction Selectivity and Its Rationale.
Type de publication
Article de revue
Année de publication
2014
Revue
J. Org. Chem.
Volume
79
Pagination
3414–3426
ISSN
0022-3263
Soumis le 12 avril 2018