Oxidation-Initiated Cyclizations of Pentadienyl Ethers: An Alternative Entry to the Nazarov Reaction.

Fradette, Ryan J; Kang, Minkyu; West, F G

Fradette, Ryan J; Kang, Minkyu; West, F G.

Afiliação

Fradette RJ; Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, T6G 2G2, Canada.
Kang M; Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, T6G 2G2, Canada.
West FG; Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, T6G 2G2, Canada.

Angew Chem Int Ed Engl ; 56(22): 6335-6338, 2017 05 22.

Article em En | MEDLINE | ID: mdl-28407344

ABSTRACT

ABSTRACT

Oxidation-initiated Nazarov reactions of 1,4-pentadien-3-yl ethers take place in the presence of DDQ. Termination by regioselective elimination preserves both stereocenters created during electrocyclization, providing cyclopentanone products bearing an exocyclic methylene unit. Use of catalytic DDQ with MnO2 as terminal oxidant is also described.

Palavras-chave

Nazarov cyclization; electrocyclic reactions; oxidation; quinones; synthetic methods

Texto completo

Imprimir

XML

PubMed Links

Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Ano de publicação: 2017 Tipo de documento: Article País de afiliação: Canadá

Texto completo

Imprimir

XML

PubMed Links

Buscar no Google