Catalytic enantioselective Diels-Alder reaction by self-assembly of the components on a Lewis acid template.
Thermal Diels-Alder reaction of 2,4-hexadienol with methyl acrylate is unselective. By simultaneous coordination of diene and dienophile to a chiral bimetallic Lewis acid catalyst, a LACASA-DA reaction occurs with complete control of regio-, diastereo-, and enantioselectivity to give a single adduct. [reaction: see text]
Ward
Dale E
DE
Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, SK, S7N 5C9 Canada. Dale.Ward@usask.ca
Souweha
Michael Santos
MS