Diels–Alder reaction of optically active (E)-γ-keto-α,β-unsaturated p-tolylsulfoxides with cyclopentadiene

Autor:	Mario Ordóñez, Victor Guerrero de la Rosa, J. M. Llera, Felipe Alcudia
Rok vydání:	2004
Předmět:	Cyclopentadiene Stereochemistry Organic Chemistry Diastereomer Optically active Biochemistry Catalysis chemistry.chemical_compound chemistry Drug Discovery Reactivity (chemistry) Lewis acids and bases Selectivity Diels–Alder reaction
Zdroj:	Tetrahedron. 60:871-875
ISSN:	0040-4020
Popis:	The Diels–Alder reaction of enantiomerically pure (E)-γ-keto-α,β-unsaturated p-tolylsulphoxides 3 with cyclopentadiene give four easily separable diastereomers. The effect of several Lewis acids on the reaction was studied, finding a high endo selectivity with respect to the carbonyl group and moderate π-diastereoselectivity using BF3·Et2O as catalyst. The reactivity of compounds 3 as well as their endo selectivity are both higher than those observed for the corresponding (E)-3-sulfinylacrylates.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::149d739fe418f5585b9488d9636530c0 https://doi.org/10.1016/j.tet.2003.11.047 Zobrazit plný text záznamu Full Text from ScienceDirect