Gold()-catalyzed nucleophilic cyclization of β-monosubstituted -(alkynyl)styrenes: a combined experimental and computational study

The stereospecific gold( i )-catalyzed nucleophilic cyclization of β-monosubstituted o -(alkynyl)styrenes to produce C-1 functionalized 1 H -indenes including challenging substrates and nucleophiles, such as β-(cyclo)alkyl-substituted o -(alkynyl)styrenes and a variety of alcohols as well as selecte...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-11, Vol.17 (46), p.9924-9932
Main Authors: Virumbrales, Cintia, Solas, Marta, Suárez-Pantiga, Samuel, Fernández-Rodríguez, Manuel A, Marín-Luna, Marta, López, Carlos Silva, Sanz, Roberto
Format: Article
Language:English
Online Access:Get full text
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Summary:The stereospecific gold( i )-catalyzed nucleophilic cyclization of β-monosubstituted o -(alkynyl)styrenes to produce C-1 functionalized 1 H -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. The diastereospecific 5- endo cyclization of β-monosubstituted o -(alkynyl)styrenes to 1-functionalized-1 H -indenes is reported. The regiospecific generation of a cyclopropyl gold carbene intermediate is also supported by DFT calculations.
ISSN:1477-0520
1477-0539
DOI:10.1039/c9ob02126d