Gold(i)-catalyzed diastereoselective synthesis of 1-α-oxybenzyl-1H-indenes

The gold(i)-catalyzed oxycyclization of β-aryl monosubstituted o-(alkynyl)styrenes gives rise to 1-α-methoxy or 1-α-hydroxybenzyl-1H-indenes in a diastereospecific way. In contrast to β,β-disubstituted o-(alkynyl)styrenes, the stereochemical outcome of this process, diastereospecific reaction suppor...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018-04, Vol.16 (15), p.2623-2628
Main Authors: Virumbrales, Cintia, Suárez-Pantiga, Samuel, Solas, Marta, Fernández-Rodríguez, Manuel A, Sanz, Roberto
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemical synthesis
Gold
Styrenes
Online Access:Get full text
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Summary:The gold(i)-catalyzed oxycyclization of β-aryl monosubstituted o-(alkynyl)styrenes gives rise to 1-α-methoxy or 1-α-hydroxybenzyl-1H-indenes in a diastereospecific way. In contrast to β,β-disubstituted o-(alkynyl)styrenes, the stereochemical outcome of this process, diastereospecific reaction supports the higher contribution of a gold intermediate with a cyclopropylcarbene-like character.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob00406d