Projects per year
Abstract
We report a method for the synthesis of chiral vicinal chloroamines via asymmetric protonation of catalytically generatedprochiral chloroenamines using chiral Brønsted acids. The processis highly enantioselective, with the origin of asymmetry and catalystsubstituent effects elucidated by DFT calculations. We show theutility of the method as an approach to the synthesis of a broadrange of heterocycle-substituted aziridines by treatment of thechloroamines with base in a one-pot process, as well as the utility ofthe process to allow access to vicinal diamines.
Original language | English |
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Article number | e202200060 |
Number of pages | 6 |
Journal | Chemistry - A European Journal |
Volume | 28 |
Issue number | 16 |
Early online date | 23 Feb 2022 |
DOIs | |
Publication status | Published - 16 Mar 2022 |
Keywords
- Asymmetric catalysis
- Aziridine
- Bronstead acid
- Chloroamine
- Heterocycles
Fingerprint
Dive into the research topics of 'Asymmetric synthesis of heterocyclic chloroamines and aziridines by enantioselective protonation of catalytically generated enamines'. Together they form a unique fingerprint.Projects
- 3 Finished
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Accessing Pharmacophoric Space: Accessing Pharmacophoric Space Via Asymmetric Protonation
Watson, A. J. B. (PI)
1/10/19 → 30/09/22
Project: Standard
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Must reductive elimination be the produc: Must reductive elimination be the product-determining event?
Watson, A. J. B. (PI)
1/05/19 → 30/04/21
Project: Standard
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Chemoselective cross-coupling: Chemoselective cross-coupling via control of anion metathesis at Pd(II)
Watson, A. J. B. (PI)
1/07/18 → 31/08/22
Project: Standard
Datasets
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Dataset underpinning "Asymmetric synthesis of heterocyclic chloroamines and aziridines by enantioselective protonation of catalytically generated enamines"
Watson, A. J. B. (Creator), University of St Andrews, 4 Feb 2022
DOI: 10.17630/816af4fa-ef6a-4043-b0f9-b88f4f8a47f1
Dataset
File -
CCDC 2111088 - 2111089: Experimental Crystal Structure Determination
McLean, L. A. (Creator), Ashford, M. W. (Creator), Fyfe, J. W. B. (Creator), Slawin, A. M. Z. (Creator), Leach, A. G. (Creator) & Watson, A. J. B. (Creator), Cambridge Crystallographic Data Centre, 2022
DOI: 10.5517/ccdc.csd.cc28vrmj, https://dx.doi.org/10.5517/ccdc.csd.cc28vrnk
Dataset