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Asymmetric and Geometry-Selective α-Alkenylation of α-Amino Acids

Research output: Contribution to journalArticle

Original languageEnglish
Pages (from-to)2418-2422
Number of pages5
JournalAngewandte Chemie - International Edition
Issue number8
Early online date2 Jan 2019
DateAccepted/In press - 8 Dec 2018
DateE-pub ahead of print - 2 Jan 2019
DatePublished (current) - 18 Feb 2019


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 [18]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.

    Research areas

  • DFT calculations, quaternary amino acids, rearrangement, stereodivergence, α-alkenylation

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