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

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Original languageEnglish
Pages (from-to)2418-2422
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number8
Early online date2 Jan 2019
DOIs
DateAccepted/In press - 8 Dec 2018
DateE-pub ahead of print - 2 Jan 2019
DatePublished (current) - 18 Feb 2019

Abstract

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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    Rights statement: This is the author accepted manuscript (AAM). The final published version (version of record) is available online via Wiley at https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201813984. Please refer to any applicable terms of use of the publisher.

    Accepted author manuscript, 1 MB, PDF-document

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