Virumbrales et al. Org Biomol Chem. 2018;16(15):2623-2628. Gold(i)-catalyzed diastereoselective synthesis of 1-α-oxybenzyl-1H-indenes.

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

Área de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, Spain.

arsd@ubu.es

Abstract

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.