Instituto de Química Orgánica General, Consejo Superior de Investigaciones Científicas (IQOG-CSIC) , Juan de la Cierva 3, 28006 Madrid, Spain.
Centro de Innovación en Química Avanzada (ORFEO-CINQA), Facultad de Química, Universidad Complutense , 28040 Madrid, Spain.
J Org Chem. 2017 Jul 21;82(14):7546-7554. doi: 10.1021/acs.joc.7b01273. Epub 2017 Jul 5.
An unprecedented stereoselective domino reaction of 1,6-enynes with an aryl ring at C3-C4 in the presence of gold(I) catalysts at low temperature is described. This process involves a novel 5-exo-dig cycloisomerization-dimerization sequence to afford formal Diels-Alder adducts that undergo a smooth gold-catalyzed double bond migration at room temperature. In addition, the first examples of the gold mesoionic carbene mediated [2+2+2] cycloaddition of these enynes with benzaldehyde are reported.
本文描述了在低温下金（I）催化剂存在下，1,6-烯炔与 C3-C4 芳环的前所未有的立体选择性串联反应。该过程涉及新颖的 5-exo-dig 环异构化-二聚化序列，以提供形式 Diels-Alder 加合物，这些加合物在室温下经历金催化的双键迁移。此外，还报道了首例这些烯炔与苯甲醛的金偕内酰胺介导的[2+2+2]环加成反应。
