58929-89-8Relevant academic research and scientific papers
Asymmetric Aminations and Kinetic Resolution of Acyclic α-Branched Ynones
He, Faqian,Shen, Guosong,Yang, Xiaoyu
supporting information, p. 15 - 20 (2021/11/20)
An efficient method for asymmetric synthesis of acyclic α-tertiary amine derivatives has been achieved through enantioselective aminations of α-branched ynones with azodicarboxylates enabled by chiral phosphoric acid catalysis. Moreover, kinetic resolution of racemic starting material was realized under these conditions, which gave access to valuable enantioenriched α-substituted ketones. A wide array of α-aryl and alkyl-substitutions, and the substituted alkynyl groups were well compatible with this method, producing both the amination products and the recovered ketones with good to high enantioselectivities.
Palladium-catalyzed α,β-dehydrogenation of acyclic ester equivalents promoted by a novel electron deficient phosphinooxazoline ligand
Fulton, Tyler J.,Wu, Brenda,Alexy, Eric J.,Zhang, Haiming,Stoltz, Brian M.
supporting information, p. 4104 - 4109 (2019/06/20)
A unique example of Pd-catalyzed decarboxylative dehydrogenation of fully substituted N-acyl allyl enol carbonates is enabled by a new electron deficient phosphinooxazoline (PHOX) ligand. The reaction proceeds from the Z-enol carbonate to provide dehydrogenation products exclusively in high E/Z selectivity, while the E-enol carbonate provides the α-allylation product with only minor dehydrogenation. The reaction proceeds with a broad scope of Z-enol carbonates derived from N-acyl indoles to furnish acyclic formal α,β-unsaturated ester equivalents.
Synthesis of α-aryl esters and nitriles: Deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids
Wu, Guojiao,Deng, Yifan,Wu, Chaoqiang,Zhang, Yan,Wang, Jianbo
supporting information, p. 10510 - 10514 (2016/02/18)
Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds into C(sp3)-C(sp2) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. Touch base: A transition-metal-free protocol for the synthesis of α-aryl esters and nitriles by deaminative coupling is presented. Strong bases and transition-metal catalysts are not needed. The new synthetic method uses readily available starting materials and demonstrates wide substrate scope.
