Transmetalation of Z-telluroenynes: stereoselective synthesis of Z-enynols and their application in palladium-catalyzed cyclization

Caroline C Schneider; Helton Caldeira; Bibiana M Gay; Davi F Back; Gilson Zeni

doi:10.1021/ol902896x

Transmetalation of Z-telluroenynes: stereoselective synthesis of Z-enynols and their application in palladium-catalyzed cyclization

Org Lett. 2010 Mar 5;12(5):936-9. doi: 10.1021/ol902896x.

Authors

Caroline C Schneider¹, Helton Caldeira, Bibiana M Gay, Davi F Back, Gilson Zeni

Affiliation

¹ Laboratório de Síntese, Reatividade, Avaliação Farmacológica e Toxicológica de Organocalcogênios, and Laboratório de Materiais Inorgânicos, CCNE, UFSM, Santa Maria, Rio Grande do Sul 97105-900, Brazil.

PMID: 20131828
DOI: 10.1021/ol902896x

Abstract

The synthesis of various Z-enynols via reaction of vinyllithium intermediate with aldehydes and ketones is described. The subsequent cyclization of a wide variety of Z-enynols afforded substituted furans and dihydrofurans with high regioselectivity under mild reaction conditions.

Publication types

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

MeSH terms

Aldehydes / chemistry
Alkynes / chemistry*
Catalysis
Cyclization
Furans / chemical synthesis*
Furans / chemistry*
Ketones / chemistry
Palladium / chemistry*
Stereoisomerism

Substances

Aldehydes
Alkynes
Furans
Ketones
Palladium