An Enamide-Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans
Philipp Kramer1, Jennifer Grimmer1, Michael Bolte2
1Department of Organic Chemistry, Technical University Kaiserslautern, Erwin-Schrödinger-Strasse Geb. 54, 67663, Kaiserslautern, Germany.
Abstract:
A novel method for the highly stereoselective synthesis of tetrahydropyrans is reported. This domino reaction is based on a twofold addition of enamides to aldehydes followed by a subsequent cyclization and furnishes fully substituted tetrahydropyrans in high yields. Three new σ-bonds and five continuous stereogenic centers are formed in this one-pot process with a remarkable degree of diastereoselectivity. In most cases, the formation of only one out of 16 possible diastereomers is observed. Two different stereoisomers can be accessed in a controlled fashion starting either from an E- or a Z-configured enamide.
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