Stereoselective Synthesis of Polysubstituted Tetrahydropyranones via Acid-Promoted Cyclization of β-Silyl-γ-ethylidene-γ-butyrolactones with Aldehydes and Ketones.

4-Butyrolactone Aldehydes Cyclization Ketones Lewis Acids Stereoisomerism

Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
03 09 2021
Historique:
pubmed: 14 8 2021
medline: 25 2 2023
entrez: 13 8 2021
Statut: ppublish

Résumé

β-Silyl-γ-ethylidene-γ-butyrolactone upon one-pot treatment with aldehydes and ketones in the presence of Lewis acids underwent a tandem Hosomi-Sakurai/Prins cyclization to give polysubstituted tetrahydropyranones stereoselectively. Various aldehydes and ketones can be used in this reaction to produce the corresponding tetrahydropyranones. The optical purity of the starting γ-butyrolactone was substantially retained in the resulting tetrahydropyranones.

Identifiants

DOI: 10.1021/acs.joc.1c01284 PMID: 34387502
pubmed: 34387502
doi: 10.1021/acs.joc.1c01284
doi:

Substances chimiques

Aldehydes 0
Ketones 0
Lewis Acids 0
4-Butyrolactone OL659KIY4X

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

11884-11894

Auteurs

Shoma Ariyoshi (S)

Division of Molecular Materials Science, Graduate School of Science, Osaka City University, Sugimoto, Osaka 558-8585, Sumiyoshi, Japan.

Kazuhiko Sakaguchi (K)

Division of Molecular Materials Science, Graduate School of Science, Osaka City University, Sugimoto, Osaka 558-8585, Sumiyoshi, Japan.
ORCID: 0000-0002-2364-0970

Takahiro Nishimura (T)

Division of Molecular Materials Science, Graduate School of Science, Osaka City University, Sugimoto, Osaka 558-8585, Sumiyoshi, Japan.
ORCID: 0000-0002-7032-8613

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Classifications MeSH

questionsmedicales.fr › Composés hétérocycliques › Composés hétéromonocycliques › Furanes › 4-Butyrolactone › Stereoselective Synthesis of Polysubstituted...
questionsmedicales.fr › Composés chimiques organiques › Aldéhydes › Stereoselective Synthesis of Polysubstituted...
questionsmedicales.fr › Métabolisme › Cyclisation › Stereoselective Synthesis of Polysubstituted...
questionsmedicales.fr › Composés chimiques organiques › Cétones › Stereoselective Synthesis of Polysubstituted...
questionsmedicales.fr › Composés chimiques organiques › Acides de Lewis › Stereoselective Synthesis of Polysubstituted...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes de chimie organique › Isomérie › Stéréoisomérie › Stereoselective Synthesis of Polysubstituted...