1595-70-6Relevant articles and documents
Relay Catalysis to Synthesize β-Substituted Enones: Organocatalytic Substitution of Vinylogous Esters and Amides with Organoboronates
Sundstrom, Sasha,Nguyen, Thien S.,May, Jeremy A.
supporting information, p. 1355 - 1359 (2020/02/13)
Organocatalysis was shown to facilitate conjugate additions to vinylogous esters and amides for the first time. Subsequent elimination of a β-alcohol or amine provided π-conjugated β-substituted enones. Remarkably, nucleophile addition to the electron-rich vinylogous substrates is more rapid than classical enones, forming monosubstituted products. A doubly organocatalytic (organic diol and methyl aniline) conjugate addition synthesized the products directly from alkynyl ketones. Both of these catalytic transformations are orthogonal to transition metal catalysis, allowing for good yields, easily accessible or commercially available reagents, high selectivity, reagent recovery and recyclability, facile scalability, and exceptional functional group tolerance.
Gem-Digold Acetylide Complexes for Catalytic Intermolecular [4 + 2] Cycloaddition: Having Two Gold Centers Is Better for Asymmetric Catalysis
Nanko, Masaki,Shibuya, Satoru,Inaba, Yuya,Ono, Soichiro,Ito, Shigekazu,Mikami, Koichi
supporting information, p. 7353 - 7357 (2018/10/15)
Gold(I)-catalyzed highly enantioselective intermolecular [4 + 2] cycloaddition is shown with ynones and cyclohexadiene. Various bicyclo[2.2.2]octadiene derivatives are produced in high yields (up to 99%) with good enantioselectivity (up to 96% ee). Key to the success is generation of the gem-digold terminal alkyne as a catalytic on-cycle species. As proof of the gem-digold catalysis, a positive nonlinear effect is clarified between the ee's of the ligand and the cycloadduct.
Catalytic decarboxylation of 2-alkynoic acids
Kolarovic, Andrej,Faberova, Zuzana
experimental part, p. 7199 - 7202 (2009/12/09)
(Chemical Equation Presented) A very efficient protocol enabling catalytic decarboxylation of a wide range of 2-alkynoic acids is described. The reaction conditions and the scope of the process are examined. The method is further utilized in a model decar
