91838-74-3Relevant articles and documents
Asymmetric Synthesis of Heterocyclic Chloroamines and Aziridines by Enantioselective Protonation of Catalytically Generated Enamines**
McLean, Liam A.,Ashford, Matthew W.,Fyfe, James W. B.,Slawin, Alexandra M. Z.,Leach, Andrew G.,Watson, Allan J. B.
supporting information, (2022/02/25)
We report a method for the synthesis of chiral vicinal chloroamines via asymmetric protonation of catalytically generated prochiral chloroenamines using chiral Br?nsted acids. The process is highly enantioselective, with the origin of asymmetry and catalyst substituent effects elucidated by DFT calculations. We show the utility of the method as an approach to the synthesis of a broad range of heterocycle-substituted aziridines by treatment of the chloroamines with base in a one-pot process, as well as the utility of the process to allow access to vicinal diamines.
Facile catalyst-free synthesis of 2-vinylquinolines via a direct deamination reaction occurring during Mannich synthesis
Xiao, Jichao,Huang, Ye,Song, Zilan,Feng, Wenhua
, p. 99095 - 99098 (2015/12/04)
A facile catalyst-free method for the synthesis of 2-vinylquinolines via a direct deamination reaction during Mannich synthesis has been developed. Instantaneous hydrogen transfer via a six-membered ring intermediate is proposed as a key step for the direct deamination reaction. This reaction strategy tolerates a broad substrate scope and provides a highly efficient way to synthesize 2-vinylquinolines with adequate yields.
Superacid-promoted additions involving vinyl-substituted pyrimidines, quinoxalines, and quinazolines: Mechanisms correlated to charge distributions
Zhang, Yiliang,Sheets, Matthew R.,Raja, Erum K.,Boblak, Kenneth N.,Klumpp, Douglas A.
supporting information; experimental part, p. 8467 - 8469 (2011/07/29)
The superacid-promoted reactions of vinyl-substituted N-heterocycles have been studied. Diprotonated pyrimidines, quinoxalines, and quinazolines exhibit an unusual regioelectronic effect that controls the type of addition reaction observed. Depending on the ring position of the vinyl substituent, either conjugate addition or Markovnikov addition occurs. The mode of addition has been shown to correlate well to NBO calculated charges.