175355-34-7Relevant articles and documents
An easy stereoselective access to β,γ-aziridino α-amino ester derivatives via Mannich reaction of benzophenone imines of glycine esters with N-sulfonyl α-chloroaldimines
Kiss, Lorand,Mangelinckx, Sven,Sillanpaeae, Reijo,Fueloep, Ferenc,De Kimpe, Norbert
, p. 7199 - 7206 (2007)
(Chemical Equation Presented) Mannich-type addition of benzophenone imine glycinates across newly synthesized N-(p-toluenesulfonyl) α- chloroaldimines afforded γ-chloro-α,β-diamino ester derivatives with moderate diastereoselectivity as separable mixtures of anti and syn diastereomers. The γ-chloro-α,β-diamino esters were efficiently cyclized under basic conditions to the corresponding β,γ-aziridino α-amino ester derivatives, representing a new class of conformationally constrained heterocyclic α,β-diamino acid derivatives. The relative configuration of the aziridines was determined via X-ray diffraction analysis. Mechanisms and intermediate transition states to explain the stereochemical outcome of the Mannich reaction with different substrates or under different conditions are proposed. The synthetic importance of the β,γ- aziridino α-amino ester derivatives is demonstrated by their conversion into the corresponding Boc-protected derivatives and ring opening reactions to α,β-diamino esters and a γ-amino α,β-unsaturated amino ester.
The Generation of Difluoroketenimine and Its Application in the Synthesis of α,α-Difluoro-β-amino Amides
Zhang, Rui,Zhang, Zhikun,Zhou, Qi,Yu, Lefei,Wang, Jianbo
, p. 5744 - 5748 (2019/03/28)
Fluorine-containing β-amino acids and their derivatives have attracted significant attention due to their importance in life sciences. Herein the previously unknown difluoroketenimine, the analogue of the elusive difluoroketene, has been generated by the
Palladium-Catalyzed Direct Intramolecular C-N Bond Formation: Access to Multisubstituted Dihydropyrroles
Jiang, Bing,Meng, Fei-Fan,Liang, Qiu-Ju,Xu, Yun-He,Loh, Teck-Peng
, p. 914 - 917 (2017/02/26)
A palladium-catalyzed intramolecular amination of alkenes with retention of olefin functionalization was achieved under mild reaction conditions. In the presence of palladium catalyst, the tosyl-protected amine can directly couple with a double bond to provide versatile dihydropyrrole derivatives in moderate to excellent yields.
