309757-76-4Relevant academic research and scientific papers
Enantioselective Synthesis of β-Amino Acid Derivatives Enabled by Ligand-Controlled Reversal of Hydrocupration Regiochemistry
Buchwald, Stephen L.,Guo, Sheng,Zhu, Jiaqi
, p. 20841 - 20845 (2020)
A Cu-catalyzed enantioselective hydroamination of α,β-unsaturated carbonyl compounds for the synthesis of β-amino acid derivatives was achieved through ligand-controlled reversal of the hydrocupration regioselectivity. While the hydrocupration of α,β-unsaturated carbonyl compounds to form α-cuprated species has been extensively investigated, we report herein that, in the presence of an appropriate ancillary chiral ligand, the opposite regiochemistry can be observed for cinnamic acid derivatives, leading to the delivery of the copper to the β-position. This copper can react with an electrophilic aminating reagent, 1,2-benzisoxazole, to provide enantioenriched β-amino acid derivatives, which are important building blocks for the synthesis of natural products and bioactive small molecules.
Palladium-catalyzed C-C bond formation of arylhydrazines with olefins via carbon-nitrogen bond cleavage
Zhu, Ming-Kui,Zhao, Jun-Feng,Loh, Teck-Peng
supporting information; experimental part, p. 6308 - 6311 (2012/01/06)
The unactivated carbon-nitrogen bond of various aryl hydrazines was cleaved under very mild conditions by Pd(0) with the assistance of Pd(II). The in situ generated aryl palladium complex readily takes part in the C-C bond formation with olefins. This study offered a new mode of C-Pd bond formation, which will spur the development of palladium-catalyzed cross-coupling in the future.
Asymmetric synthesis of β-haloaryl β-amino acid derivatives
Bull, Steven D.,Davies, Stephen G.,Delgado-Ballester, Santiago,Kelly, Peter M.,Kotchie, Luke J.,Gianotti, Massimo,Laderas, Mario,Smith, Andrew D.
, p. 3112 - 3121 (2007/10/03)
Lithium N-benzyl-N-α-methyl-4-methoxybenzylamide may be employed as a homochiral ammonia equivalent for the synthesis of homochiral β-haloaryl β-amino acid derivatives via a strategy involving its conjugate addition to α,β-unsaturated β-haloaryl acceptors and subsequent oxidative deprotection with ceric ammonium nitrate.
