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A novel method for the highly stereoselective synthesis of tetrahydropyrans is reported. This domino reaction is based on a two-fold 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.
This article was published in the following journal.
Name: Angewandte Chemie (International ed. in English)
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