@article{916414d07d5a469aa53aa3bdaeb2b2d2,
title = "Asymmetric Synthesis of Heterocyclic Chloroamines and Aziridines by Enantioselective Protonation of Catalytically Generated Enamines**",
abstract = "We report a method for the synthesis of chiral vicinal chloroamines via asymmetric protonation of catalytically generated prochiral chloroenamines using chiral Br{\o}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.",
keywords = "Br{\o}nsted acid, asymmetric catalysis, aziridine, chloroamine, heterocycles",
author = "McLean, {Liam A.} and Ashford, {Matthew W.} and Fyfe, {James W. B.} and Slawin, {Alexandra M. Z.} and Leach, {Andrew G.} and Watson, {Allan J. B.}",
note = "Funding Information: L.A.M. and J.W.B.F. thank EPSRC for postdoctoral funding (EP/S027165/1; EP/R025754/1). J.W.B.F. thanks the Leverhulme Trust for postdoctoral funding (RPG‐2018‐362). M.W.A. thanks the University of St Andrews for a PhD studentship. A.G.L. would like to acknowledge the assistance given by Research IT and the use of the Computational Shared Facility at The University of Manchester. Funding Information: L.A.M. and J.W.B.F. thank EPSRC for postdoctoral funding (EP/S027165/1; EP/R025754/1). J.W.B.F. thanks the Leverhulme Trust for postdoctoral funding (RPG-2018-362). M.W.A. thanks the University of St Andrews for a PhD studentship. A.G.L. would like to acknowledge the assistance given by Research IT and the use of the Computational Shared Facility at The University of Manchester. Publisher Copyright: {\textcopyright} 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH",
year = "2022",
month = mar,
day = "16",
doi = "10.1002/chem.202200060",
language = "English",
volume = "28",
journal = "Chemistry – A European Journal",
issn = "0947-6539",
publisher = "John Wiley & Sons Ltd",
number = "16",
}