771477-49-7Relevant articles and documents
Gold(I)-Catalyzed Reactions between 2-(1-Alkynyl)-2-alken-1-ones and Vinyldiazo Ketones for Divergent Synthesis of Nonsymmetric Heteroaryl-Substituted Triarylmethanes: N-versus C-Attack Paths
Kardile, Rahul Dadabhau,Liu, Rai-Shung
supporting information, p. 8229 - 8233 (2020/11/03)
Gold-catalyzed synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes using 2-(1-alkynyl)-2-alken-1-ones and vinyldiazo ketones is described. In this catalytic sequence, vinyldiazo ketones attack gold-containing 3-furylbenzyl cations to form the observed C(1)-addition products. We also note that vinyldiazo ketones can be thermally cyclized to yield pyrazole derivatives, which can react with 3-furylbenzyl cations to afford pyrazole-containing triarylmethanes, corresponding to a N(5)-addition path.
Rapid assembly of 3-azidomethylfurans from 2-(1-alkynyl)-2-alken-1-ones enabled by silver catalysis
Qian, Lei-Lei,Yi, Ruxia,Min, Xiang-Ting,Hu, Yan-Cheng,Wan, Boshun,Chen, Qing-An
, (2020/06/24)
A rapid access to useful 3-azidomethylfurans is developed via Ag(I)-catalyzed cascade annulation/azidation of 2-(1-alkynyl)-2-alken-1-ones. The salient features of the protocol include mild reaction conditions, high efficiency, broad substrate scope, and
Gold(I)-Catalyzed Highly Diastereo- and Enantioselective Cyclization–[4+3] Annulation Cascades between 2-(1-Alkynyl)-2-alken-1-ones and Anthranils
Chao, Tzu-Hsuan,Cheng, Mu-Jeng,Kardile, Rahul Dadabhau,Liu, Rai-Shung
supporting information, p. 10396 - 10400 (2020/04/29)
This work reports gold-catalyzed [4+3]-annulations of 2-(1-alkynyl)-2-alken-1-ones with anthranils to yield epoxybenzoazepine products with excellent exo-diastereoselectivity (dr>25:1). The utility of this new gold catalysis is manifested by applicable substrates over a broad scope. More importantly, the enantioselective versions of these [4+3]-cycloadditions have been developed satisfactorily with chiral gold catalysts under ambient conditions (DCM, 0 °C); the ee levels range from 88.0–99.9 %. With DFT calculations, we postulate a stepwise pathway to rationalize the preferable exo-stereoselection.
Chiral Phosphine–Phosphite Ligands in Asymmetric Gold Catalysis: Highly Enantioselective Synthesis of Furo[3,4-d]-Tetrahydropyridazine Derivatives through [3+3]-Cycloaddition
Du, Qingwei,Neud?rfl, J?rg-Martin,Schmalz, Hans-Günther
supporting information, p. 2379 - 2383 (2018/01/27)
The AuI-catalyzed reaction of 2-(1-alkynyl)-2-alken-1-ones with azomethine imines regio- and diastereoselectively affords furo[3,4-d]tetrahydropyridazines in a tandem cyclization/intermolecular [3+3]-cycloaddition process under mild conditions.
Organocatalytic Formation of Chiral Trisubstituted Allenes and Chiral Furan Derivatives
Poulsen, Pernille H.,Li, Yang,Lauridsen, Vibeke H.,J?rgensen, Danny K. B.,Palazzo, Teresa A.,Meazza, Marta,J?rgensen, Karl Anker
supporting information, p. 10661 - 10665 (2018/07/30)
A novel reaction that provides chiral allenes by amino catalytic activation of either aldehydes or α,β-unsaturated aldehydes for reaction with alkynyl-substituted enones is presented. The reaction forms a variety of trisubstituted allenes in high yields a
Chemoselective C-C bond cleavage of epoxide motifs: Gold(I)-catalyzed diastereoselective [4+3] cycloadditions of 1-(1-Alkynyl)oxiranyl ketones and nitrones
Wang, Tao,Zhang, Junliang
scheme or table, p. 86 - 90 (2011/03/20)
Cutting carbon! A novel facile strategy for the C-C bond cleavage of oxiranyl ketones has been developed. Carbophilic gold(I) activation of the alkyne side chain mediates a heterocyclization and subsequent C-C bond cleavage (see scheme).
AuCl3-catalyzed synthesis of highly substituted furans from 2-(1-alkynyl)-2-alken-1-ones
Yao, Tuanli,Zhang, Xiaoxia,Larock, Richard C.
, p. 11164 - 11165 (2007/10/03)
Highly substituted furans have been synthesized by the reaction of 2-(1-alkynyl)-2-alken-1-ones and various nucleophiles under very mild reaction conditions in good to excellent yields. Gold and some other transition metals are efficient catalysts for thi
