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

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Lactams
epoxidation
metathesis
nucleophiles
closing
attack
activation
chemistry
rings
Stereoselectivity
Regioselectivity
Nucleophiles
Epoxidation
Cyclization
atoms
Serine
Chemical activation
Derivatives
Atoms

Keywords

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

Cite this

Schurgers, Ben ; Wouters, Johan ; De Blieck, Ann ; Van Lommen, Guy ; Menet, Christel ; Verniest, Guido. / Regio‐and Diastereoselective Functionalization of 3‐Amino‐hexahydrooxazoninones. In: European Journal of Organic Chemistry. 2019 ; Vol. 2019, No. 1. pp. 36-40.
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Regio‐and Diastereoselective Functionalization of 3‐Amino‐hexahydrooxazoninones. / Schurgers, Ben; Wouters, Johan; De Blieck, Ann; Van Lommen, Guy; Menet, Christel; Verniest, Guido.

In: European Journal of Organic Chemistry, Vol. 2019, No. 1, 10.01.2019, p. 36-40.

Research output: Contribution to journalArticle

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