Asymmetric Synthesis of Functionalized Dihydro- and Tetrahydropyrans via an Organocatalytic Domino Michael–Hemiacetalization Reaction

Abstract

Starting from α-hydroxymethyl nitroalkenes and various 1,3-dicarbonyl compounds, a one-pot organocatalyzed diastereo- and enantioselective synthesis of polyfunctionalized dihydro- and tetrahydropyran derivatives via a domino Michael-hemiacetalization sequence is reported. The title compounds bearing a variety of functional groups can be synthesized in this way in good yields (59–91%) and with moderate to excellent diastereoselectivities (26–98% de) and enantioselectivities (71–99% ee).

Key words

organocatalysis - domino reaction - one-pot reaction - tetrahydropyrans - hydrogen bonding

• References


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