Regio‐and Diastereoselective Functionalization of 3‐Amino‐hexahydrooxazoninones

Ben Schurgers, Johan Wouters, Ann De Blieck, Guy Van Lommen, Christel Menet, Guido Verniest

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Abstract

The regio- and diastereoselectivity of transformations of nine-membered lactams with a Z double bond in the cyclic tether towards building blocks for medicinal chemistry was evaluated. To this end, 3-aminohexahydrooxazoninones were synthesized using a standard ring-closing metathesis (RCM) approach of easily available O,N-bisallylated serine derivatives. The obtained Z double bond in the medium sized lactam was used as a handle to evaluate the stereoselectivity of electrophile induced transformations. It was shown that dibromination and electrophilic activation by NBS followed by attack of O-nucleophiles proceeded in a diastereoselective manner. Cyclization of obtained bromohydrins and face-selective epoxidation gave access to both diastereomers of the epoxidized lactams. Finally, a Heck-reaction of a bromobenzyl moiety at the lactam N-atom with the Z-double bond resulted in the diastereoselective formation of bicyclic bridged nine-membered lactams.

Original languageEnglish
Pages (from-to)36-40
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number1
DOIs
Publication statusPublished - 10 Jan 2019

Keywords

  • Cyclization
  • Diastereoselectivity
  • Heck reaction
  • Medium-ring compounds
  • Metathesis

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    CCDC 1847423: Experimental Crystal Structure Determination

    Schurgers, B. (Creator), WOUTERS, J. (Contributor), De Blieck, A. (Creator), Van Lommen, G. (Creator), Menet, C. (Creator) & Verniest, G. (Creator), University of Namur, 10 Jan 2019

    Dataset

    CCDC 1847422: Experimental Crystal Structure Determination

    Schurgers, B. (Creator), WOUTERS, J. (Contributor), De Blieck, A. (Creator), Van Lommen, G. (Creator), Menet, C. (Creator) & Verniest, G. (Creator), University of Namur, 10 Jan 2019

    Dataset

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