Abstract
AbstractA 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.
Highlights
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 sbonds and five continuous stereogenic centers are formed in this one-pot process with a remarkable degree of diastereoselectivity
Two different stereoisomers can be accessed in a controlled fashion starting either from an E- or a Z-configured enamide
Summary
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. All other tested Lewis or Brønsted acids, such as TiCl4, SnCl4, TMSOTf, or HBF4, did not afford the tetrahydropyran product 3 a at all (entry 5).
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