Gold(I)-catalyzed diastereoselective hydroacylation of terminal alkynes with glyoxals

Angewandte Chemie
Shuai ShiA Stephen K Hashmi

Abstract

The reaction of an α-ketoaldehyde and a terminal alkyne in the presence of piperidine and a catalytic amount of AuCl delivers 1,2-dicarbonyl-3-enes, products of the formal hydroacylation of the triple bond. The scope of the method is broad; different aryl substituents on the dicarbonyl unit and on the alkyne are well tolerated. The products can be transformed selectively into vinylquinoxalines. Mechanistic studies, including isotope-labeling experiments, indicate that after an initial A(3) -type conversion to propargylic amines, a subsequent base-mediated alkyne-to-allene isomerization and a hydrolysis of the enamine substructure during the workup deliver the formal hydroacylation products.

References

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Apr 12, 2013·Chemistry : a European Journal·Shuai ShiA Stephen K Hashmi

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Citations

Feb 18, 2016·Chemical Reviews·Carmela De RisiVinicio Zanirato
Dec 23, 2016·Chemistry : a European Journal·Abdessamad GrirraneAvelino Corma
Jul 12, 2017·The Journal of Organic Chemistry·Akinobu MatsuzawaMasakatsu Shibasaki
Nov 24, 2016·Organic & Biomolecular Chemistry·Mani RamanathanShiuh-Tzung Liu
Aug 16, 2018·Organic & Biomolecular Chemistry·Alagesan MuthukumarGovindasamy Sekar
Sep 4, 2018·Chemistry : a European Journal·Abdessamad GrirraneAvelino Corma
May 19, 2017·Chemical Communications : Chem Comm·Yu-Chen HsuRai-Shung Liu
Oct 30, 2014·Chemical Communications : Chem Comm·RahulKumar Rajmani Singh, Rai-Shung Liu
Dec 16, 2017·Organic & Biomolecular Chemistry·Sadhanendu SamantaAlakananda Hajra
Jan 22, 2015·Journal of the American Chemical Society·Qing-An ChenVy M Dong
May 20, 2015·The Journal of Organic Chemistry·Kanchan MalIndrajit Das
Oct 26, 2021·Chemical Communications : Chem Comm·Guanghui WangXimei Zhao

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