1619985-29-3Relevant academic research and scientific papers
Stereoselective Synthesis of Tetrahydroquinolines via Asymmetric Domino Reaction Catalyzed by a Recyclable Ionic-Liquid-Supported Bifunctional Tertiary Amine
Tukhvatshin, Rinat S.,Kucherenko, Alexander S.,Nelyubina, Yulia V.,Zlotin, Sergei G.
supporting information, p. 7000 - 7008 (2018/12/05)
The most recyclable ionic liquid-supported bifunctional tertiary amine–squaramide organocatalyst for the asymmetric domino reaction has been found. Over this catalyst, ortho-aminochalcones protected with Tosyl or Nosyl groups underwent the aza-Michael/Michael domino reaction with nitroolefins to afford corresponding 2,3,4-trisubstituted tetrahydroquinolines as single diastereomers in nearly quantitative yield with up to 99 % ee. The catalyst was readily separated from the reaction mixture via a simple centrifugation/decantation workup and 19 times reused in the catalytic reaction without noticeable conversion or enantioselectivity reduction. The N-nosylated products proved their synthetic value for pharmacology given their facile conversion to fused pirrolidino-tetrahydroquinolines of high diastreomeric and enantiomeric purity via successive deprotection and reductive amination.
Asymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl α,β-unsaturated ketones: Construction of chiral functionalized tetrahydroquinolines
Kim, Shinae,Kang, Ki-Tae,Kim, Sung-Gon
, p. 5114 - 5121 (2014/07/08)
The diastereo- and enantioselective synthesis of 2,3,4-trisubstituted tetrahydroquinolines has been developed through organocatalytic domino aza-Michael-Michael reaction of o-N-tosylaminophenyl α,β-unsaturated ketones with nitroalkenes. This useful and simple domino process afforded diverse highly functionalized tetrahydroquinolines, some of which are not easily accessible using other methodologies, in good yields and with excellent diastereo- and enantioselectivities (up to >30:1 dr, >99% ee).
Asymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl α,β-unsaturated ketones: Construction of chiral functionalized tetrahydroquinolines
Kim, Shinae,Kang, Ki-Tae,Kim, Sung-Gon
, p. 5114 - 5121 (2014/12/10)
The diastereo- and enantioselective synthesis of 2,3,4-trisubstituted tetrahydroquinolines has been developed through organocatalytic domino aza-Michael-Michael reaction of o-N-tosylaminophenyl α,β-unsaturated ketones with nitroalkenes. This useful and simple domino process afforded diverse highly functionalized tetrahydroquinolines, some of which are not easily accessible using other methodologies, in good yields and with excellent diastereo- and enantioselectivities (up to >30:1 dr, >99% ee).
