Projects per year
Abstract
In situ generated 2-phenyl-azetidinium ylides react with boronic esters to form acyclic γ-dimethylamino tertiary boronic esters. The transformation is believed to involve the formation of a zwitterionic boronate, which subsequently undergoes ring-opening 1,2-migration, which is promoted by the relief of ring strain. Owing to the configurational instability of the initially formed ylides, which appear to be in equilibrium with the open-chain carbene form, the reaction is not stereospecific. The C-B bond of the γ-dimethylamino tertiary boronic esters can be transformed into a variety of functional groups (C-OH, C-vinyl, C-H, C-BF3), thus giving a diverse selection of 3-aryl-1-aminopropanes, which represent a privileged motif among drug molecules.
Original language | English |
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Pages (from-to) | 3241-3253 |
Number of pages | 13 |
Journal | Synthesis (Germany) |
Volume | 48 |
Issue number | 19 |
Early online date | 7 Jul 2016 |
DOIs | |
Publication status | Published - 4 Oct 2016 |
Keywords
- 3-aryl-1-aminopropanes
- azetidinium ion
- boronic esters
- borylation
- lithiation
- ring-opening
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Dive into the research topics of 'Synthesis of 3-Aryl-1-aminopropane Derivatives: Lithiation-Borylation-Ring-Opening of Azetidinium Ions'. Together they form a unique fingerprint.Projects
- 2 Finished
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3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
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Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
Aggarwal, V. K. (Principal Investigator)
14/05/12 → 13/01/18
Project: Research