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An Enamide-Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans.

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 ?-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.

SUBMITTER: Kramer P

PROVIDER: S-EPMC6772187 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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An Enamide-Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans.

Kramer Philipp P Grimmer Jennifer J Bolte Michael M Manolikakes Georg G

Angewandte Chemie (International ed. in English) 20190807 37

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. Tw ...[more]

PMID: 31298800

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