2-Hydroxyalkyl, 2-Aminoalkyl Furanes, and 2,3-Dihydrofuranes

Significance

Jørgensen and co-workers report a one-pot reaction cascade for the enantioselective synthesis of 2-hydroxyalkyl and 2-aminoalkyl furanes from α,β-unsaturated aldehydes and 1,3-dicarbonyl compounds. The one-pot procedure was carried out in a secondary amine 2 catalyzed epoxidation or aziridination/base-mediated ring opening/cyclization/acid-promoted dehydration sequence, providing various furanes 5 in good yields and high optical purity (er up to 97.5:2.5). Interrupting the reaction sequence before dehydration is also possible, and the corresponding optically active 2,3-dihydrofuranes 4 could be obtained in good yields with up to 7:1 dr and up to 99:1 er.