Synergistic catalysis: enantioselective cyclopropanation of alkylidene benzoxazoles by Pd(ii) and secondary amine catalysis. Scope, limitations and mechanistic insight

Meazza, M. ; Polo, V. (Universidad de Zaragoza) ; Merino, P. (Universidad de Zaragoza) ; Rios, R.

Resumen: The reaction of alkyl-benzoxazoles with enals has been reported using a synergistic approach. It consists of the activation of enals with a secondary amine catalyst and the activation of benzoxazoles with a metal Lewis acid. This approach has also been applied to the synthesis of cyclopropanes with excellent results. We demonstrated the applicability of this reaction in a cascade reaction (cyclopropanation + ring opening) that circumvents some of the limitations of the simple Michael addition between alkyl-benzoxazoles and enals. Finally, mechanistic studies have been reported to explain the stereoselectivity of the cyclopropanation reaction that renders an unusual cis conformation.

Idioma: Inglés

DOI: 10.1039/c7qo00858a

Año: 2018

Publicado en: Organic Chemistry Frontiers 5, 5 (2018), 806-812
ISSN: 2052-4129

Factor impacto JCR: 5.076 (2018)

Categ. JCR: CHEMISTRY, ORGANIC rank: 6 / 57 = 0.105 (2018) - Q1 - T1

Factor impacto SCIMAGO: 1.774 - Organic Chemistry (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E10
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2016-76155-R

Tipo y forma: Article (PostPrint)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)
Área (Departamento): Área Química Física (Dpto. Química Física)