Gold(i)-catalyzed nucleophilic cyclization of β-monosubstituted o-(alkynyl)styrenes: a combined experimental and computational study
- Virumbrales, Cintia
- Solas Luera, Marta
- Suarez Pantiga, Samuel
- Fernández Rodríguez, Manuel A.
- Marín Luna, Marta
- Silva López, Carlos
- Sanz Díez, Roberto
Publication date
December 2019
DOI Publisher
Royal Society of Chemistry (RSC) Journal
Organic & Biomolecular Chemistry Language
EnglishAbstract
The stereospecific gold(I)-catalyzed nucleophilic cyclization of β-monosubstituted o-(alkynyl)styrenes to produce C-1 functionalized 1H-indenes including challenging substrates and nucleophiles, such as β-(cyclo)alkyl-substituted o-(alkynyl)styrenes and a variety of alcohols as well as selected electron-rich aromatics, is reported. DFT calculations support the stereochemical outcome of the process that involves the formation of a key cyclopropyl gold carbene intermediate through a regiospecific 5-endo cyclization.Ministerio de Economía y Competitividad (MINECO) and FEDER (CTQ2016-75023-C2-1-P and 2-P), and Junta de Castilla y León and FEDER (BU291P18) and Xunta de Galicia (ED431C 2017/70 and ED431E 2018/07
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