Asymmetric Gold(I)‐Catalyzed Tandem Hydroarylation–Nazarov Cyclization: Enantioselective Access to Cyclopentenones

Autor:	Marta Solas, Samuel Suárez‐Pantiga, Roberto Sanz
Rok vydání:	2022
Předmět:	Cyclopentenones Chemistry Organic Química orgánica Hydroarylation Gold General Chemistry General Medicine Asynmetric Catalysis Catalysis Nazarov Cyclization
Zdroj:	Angewandte Chemie. 134
ISSN:	1521-3757 0044-8249
DOI:	10.1002/ange.202207406
Popis:	The asymmetric synthesis of cyclopentachromenones from gold-catalyzed reaction of readily available skipped alkenynones is described. This cascade reaction involves an initial anti-Michael hydroarylation of the ynone moiety to form a gold-functionalized dialkenylketone intermediate, followed by a Nazarov cyclization that proceeds in an unprecedented enantioselective manner. Excellent enantiomeric ratios and chemical yields are obtained under mild reaction conditions. We gratefully acknowledge Ministerio de Ciencia e Innovación and FEDER (CTQ2016-75023-C2-1-P and PID2020- 115789GB-C21), and Junta de Castilla y León and FEDER (BU291P18 and BU049P20) for financial support. The project leading to these results has received funding from “la Caixa” Foundation, under the Agreement LCF/PR/ PR18/51130007> (CAIXA-UBU001). M.S. and S.S.-P. thank Junta de Castilla y León (Consejería de Educación) and Fondo Social Europeo (ESF+) for a predoctoral and a postdoctoral contract, respectively.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::44198e3d8c28efe698c72a459f965ce8 https://doi.org/10.1002/ange.202207406 Zobrazit plný text záznamu