132233-78-4Relevant academic research and scientific papers
Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals
Pati, Kamalkishore,Dos Passos Gomes, Gabriel,Harris, Trevor,Alabugin, Igor V.
supporting information, p. 928 - 931 (2016/03/15)
Selective gold(I)-catalyzed rearrangement of aromatic methoxypropynyl acetals leads to fused catechol ethers (1,2-dialkoxynapthalenes) in excellent yields. Furthermore, this process extends to the analogous heterocyclic and aliphatic substrates. Alkyne activation triggers nucleophilic addition of the acetal oxygen that leads to an equilibrating mixture of oxonium ions of similar stability. This mixture is "kinetically self-sorted" via a highly exothermic cyclization. Selective formation of 1,2-dialkoxy naphthalenes originates from chemoselective aromatization of the cyclic intermediate via 1,4-elimination of methanol.
Enantioselective intramolecular propargylic amination using chiral copper-pybox complexes as catalysts
Shibata, Masashi,Nakajima, Kazunari,Nishibayashi, Yoshiaki
supporting information, p. 7874 - 7877 (2014/07/08)
Intramolecular propargylic amination of propargylic acetates bearing an amino group at the suitable position in the presence of chiral copper-pybox complexes proceeds enantioselectively to give optically active 1-ethynyl-isoindolines (up to 98% ee). The method described in this communication provides a useful synthetic approach to the enantioselective preparation of nitrogen containing heterocyclic compounds with an ethynyl group at the α-position. This journal is the Partner Organisations 2014.
Application of the intramolecular isomerisation - Aldolisation from allylic alcohols and allylic silyl ethers to the synthesis of indanones and indenones
Petrignet, Julien,Roisnel, Thierry,Gree, Rene
, p. 7374 - 7384 (2008/03/14)
A new access to indanones was discovered through a one-step nickel or iron-mediated transposition of 2-hydroxyisobenzofurans. Starting from the corresponding silylenol ethers, a new one-pot tandem isomerisation-Mukaiyama aldol process was also developed. These versatile strategies will be useful for the preparation of various types of indanones and indenones.
