99845-86-0Relevant academic research and scientific papers
Cycloisomerization of Conjugated Allenones into Furans under Mild Conditions Catalyzed by Ligandless Au Nanoparticles
Zorba, Leandros,Kidonakis, Marios,Saridakis, Iakovos,Stratakis, Manolis
supporting information, p. 5552 - 5555 (2019/08/01)
Au nanoparticles supported on TiO2 (1 mol %) catalyze the quantitative cycloisomerization of conjugated allenones into furans under very mild conditions. The reaction rate is accelerated by adding acetic acid (1 equiv), but the acid does not participate in the protodeauration step as in the corresponding Au(III)-catalyzed transformation. The process is purely heterogeneous, allowing thus the recycling and reuse of the catalyst effectively in several runs.
Generation and Rearrangement of N,O-Dialkenylhydroxylamines for the Synthesis of 2-Aminotetrahydrofurans
Son, Jongwoo,Reidl, Tyler W.,Kim, Ki Hwan,Wink, Donald J.,Anderson, Laura L.
, p. 6597 - 6600 (2018/05/03)
A new diastereoselective route to 2-aminotetrahydrofurans has been developed from N,O-dialkenylhydroxylamines. These intermediates undergo a spontaneous C?C bond-forming [3,3]-sigmatropic rearrangement followed by a C?O bond-forming cyclization. A copper-catalyzed N-alkenylation of an N-Boc-hydroxylamine with alkenyl iodides, and a base-promoted addition of the resulting N-hydroxyenamines to an electron-deficient allene, provide modular access to these novel rearrangement precursors. The scope of this de novo synthesis of simple nucleoside analogues has been explored to reveal trends in diastereoselectivity and reactivity. In addition, a base-promoted ring-opening and Mannich reaction has been discovered to covert 2-aminotetrahydrofurans to cyclopentyl β-aminoacid derivatives or cyclopentenones.
Synthesis of 2-vinylbenzofurans via the copper-catalyzed multicomponent reactions involving an oxa-michael/arylation/vinylation cascade
Wan, Jie-Ping,Wang, Hang,Liu, Yunyun,Ding, Hanfeng
supporting information, p. 5160 - 5163 (2014/12/11)
2-Vinylbenzofurans have been synthesized via the copper-catalyzed one-pot, three-component reactions of o-iodophenols, in situ generated allenes, and dichloromethane. Cascade transformation of oxa-Michael addition, C-arylation, and sp3C-H/spsu
Copper-catalyzed, C-C coupling-based one-pot tandem reactions for the synthesis of benzofurans using o-iodophenols, acyl chlorides, and phosphorus ylides
Liu, Yunyun,Wang, Hang,Wan, Jie-Ping
, p. 10599 - 10604 (2015/02/19)
One-pot reactions involving acyl chlorides, phosphorus ylides, and o-iodophenols with copper catalysis have been established for the rapid synthesis of functionalized benzofurans. With all of these easily available and stable reactants, the construction o
Tandem reactions of 1,2-allenic ketones leading to substituted benzenes and α,β-unsaturated nitriles
Zhang, Xinying,Jia, Xuefei,Fang, Liangliang,Liu, Nan,Wang, Jianji,Fan, Xuesen
supporting information; experimental part, p. 5024 - 5027 (2011/11/12)
One-pot double Michael addition/intramolecular aldol reaction/ decarboxylation of 1,2-allenic ketones with cyanoacetate offers an efficient and convenient approach to highly functionalized benzenes. With 2-substituted cyanoacetates, the reaction proceeds via a different tandem process to afford α,β-unsaturated nitriles effectively.
