Both E- and Z-N′-alkenyl urea derivatives of imidazolidinones may be formed selectively from enantiopure α-amino acids. Generation of their enolate derivatives in the presence of K + and crown-6 induces intramolecular migration of the alkenyl group from N′ to Cα with retention of double bond geometry. DFT calculations indicate a partially concerted substitution mechanism. Hydrolysis of the enantiopure products under acid conditions reveals quaternary α-alkenyl amino acids with stereodivergent control of both absolute configuration and double bond geometry.
|Number of pages||5|
|Journal||Angewandte Chemie - International Edition|
|Early online date||2 Jan 2019|
|Publication status||Published - 18 Feb 2019|
- DFT calculations
- quaternary amino acids
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Professor Jonathan Clayden
- School of Chemistry - Professor of Chemistry
Dr Natalie Fey
- School of Chemistry - Associate Professor
- Supramolecular and Mechanistic Chemistry
- Computational and Theoretical Chemistry
Person: Academic , Member