Asymmetric Synthesis of Heterocyclic Chloroamines and Aziridines by Enantioselective Protonation of Catalytically Generated Enamines**
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.
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)
Lewis Acid Catalysed Cyclisation and Halogen Exchange Reactions of 1,1'-Biphenyl-2-yl Isocyanide Dihalides
1,1'-Biphenyl-2-yl isocyanide dichloride and dibromide undergo unprecedented intramolecular Friedel-Crafts type cyclisation reactions catalysed by various Lewis acids affording useful synthetic methods for otherwise difficult to access 6-chloro- and 6-bromo-phenanthridines; nucleophilic displacement reactions of the latter and halogen exchange reactions of 1,1'-biphenyl-2-yl isocyanide dichloride and dibromide are also described.
Currie, Kevin S.,Tennant, George
p. 2295 - 2296
(2007/10/02)
SYNTHESE DANS LA SERIE DES PHENANTHRIDINES. IV. PREPARATION DE NOUVEAUX RADIOPROTECTEURS A MOTIF PHENANTHRIDINE
New phenanthridines substituted in the 6-position by a β-aminoethylthiol chain have been synthesized.These new products are easily obtained from 6-methylphenanthridine by a Mannich reaction or from 6-bromophenanthridine by substitution.From the 6-carboxaldehydophenanthridine and the β-aminoethylthiol, the corresponding thiazolidine or imine are obtained.These compounds are likely to be new radioprotectors.
Lion, Claude,Boukou-Poba, Jean-Paul,Charvy, Claude
p. 169 - 174
(2007/10/02)
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