53724-05-3Relevant articles and documents
Enantioselective Inverse Electron Demand (3 + 2) Cycloaddition of Palladium-Oxyallyl Enabled by a Hydrogen-Bond-Donating Ligand
Zheng, Yin,Qin, Tianzhu,Zi, Weiwei
supporting information, p. 1038 - 1045 (2021/01/25)
Cycloaddition reactions between oxyallyl cations and alkenes are important transformations for the construction of ring systems. Although (4 + 3) cycloaddition reactions of oxyallyl cations are well-developed, (3 + 2) cycloadditions remain rare, and an as
A C-H Insertion Approach to Functionalized Cyclopentenones
Wang, Youliang,Zarca, Maxence,Gong, Liu-Zhu,Zhang, Liming
supporting information, p. 7516 - 7519 (2016/07/06)
Cyclopentenones are synthetically versatile structures, and their straightforward construction from alkynone substrates by employing synthetically streamlining C-H insertion is conceptually appealing and of high synthetic potential. But, its implementation is very limited. Herein we report a Au-catalyzed version, which affords 2-bromocyclopent-2-en-1-ones with a broad scope and synthetically desirable diastereoselectivities. The proposed key intermediate capable of the observed insertion into unactivated C-H bonds is a fully functionalized gold vinylidene, which is generated via a novel intermolecular strategy. This flexible access of likely gold vinylidenes opens various opportunities to explore their versatile reactivities.
Mild propargylic oxidation using a diacetoxyiodobenzene/tert-butyl hydroperoxide protocol
Zhao, Yi,Ng, Angela Wan Ting,Yeung, Ying-Yeung
, p. 4370 - 4372 (2014/07/22)
A mild propargylic oxidation of alkynes is reported using a diacetoxyiodobenzene/tert-butyl hydroperoxide (DIB/TBHP) protocol. The reactions proceed smoothly at 0 °C and a number of α,β-unsaturated alkynoic ketones are obtained.
Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings
Ardolino, Michael J.,Morken, James P.
, p. 8770 - 8773 (2012/07/02)
The palladium-catalyzed cross-coupling of chiral propargyl acetates and allyl boronates delivers chiral 1,5-enynes with excellent levels of chirality transfer and can be applied across a broad range of substrates.
meso-Phbox-Pd(II) catalyzed tandem carbonylative cyclization of 1-ethynyl-1-propargyl acetate
Kato, Keisuke,Teraguchi, Ryuhei,Motodate, Satoshi,Uchida, Akira,Mochida, Tomoyuki,Peganova, Tat'yana A.,Vologdin, Nikolai V.,Akita, Hiroyuki
supporting information; experimental part, p. 3687 - 3689 (2009/02/05)
Palladium(II) catalyzed carbonylation of 1-ethynyl-1-propargyl acetate 1 is described; in the absence of the bisoxazoline (box) ligand, the second triple bond did not react, affording cyclic orthoesters 3 and 4. The use of meso-Phbox-Pd(II) strikingly changed the course of the reaction, yielding bicyclic lactone 2 by tandem carbonylative cyclization as a result of insertion of the second triple bond. The Royal Society of Chemistry.
A convenient synthesis of masked β-ketoaldehydes by the controlled addition of nucleophiles to (trimethylsilyl)ethynyl ketones
Bromidge,Entwistle,Goldstein,Orlek
, p. 487 - 494 (2007/10/02)
The controlled addition of nucleophiles to (trimethylsilyl)ethynyl ketones provides a facile route to β-ketoacetals, β-alkoxy-α,β-unsaturated ketones or vinylogous amides depending on the choice of reaction conditions.