Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 8, Pages 2418-2422Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201813984
Keywords
alpha-alkenylation; DFT calculations; quaternary amino acids; rearrangement; stereodivergence
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Funding
- ERC
- EPSRC
- EPSRC Centre for Doctoral Training in Catalysis [EP/L016443/1]
- Syngenta
- Presidential Leadership Program of Egypt
- EPSRC [EP/K03927X/1, EP/L011999/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/K03927X/1, EP/L011999/1] Funding Source: researchfish
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Both E- and Z-N '-alkenyl urea derivatives of imidazolidinones may be formed selectively from enantiopure alpha-amino acids. Generation of their enolate derivatives in the presence of K+ and [18]crown-6 induces intramolecular migration of the alkenyl group from N ' to C alpha with retention of double bond geometry. DFT calculations indicate a partially concerted substitution mechanism. Hydrolysis of the enantiopure products under acid conditions reveals quaternary alpha-alkenyl amino acids with stereodivergent control of both absolute configuration and double bond geometry.
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