A Facile Synthesis of Oxiranes Possessing Three or Four Carbonyl Groups

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Author(s): Haruyasu Asahara*, Shuhei Kikuchi, Yuto Unno, Soichi Yokoyama, Kotaro Yoshioka, Shinki Tani, Kazuto Umezu, Nagatoshi Nishiwaki*.

Journal Name: Current Organic Chemistry


Tri-carbonylated oxiranes were efficiently synthesized by condensing a vicinal tricarbonyl compound with α-bromoketones in the presence of a base. This protocol was applicable to α–bromo-β-keto esters to create tetra-carbonylated oxiranes, from which trifunctionalized bromoalkene was competitively formed. The ratio of these compounds was influenced by the solvent and reaction temperature.

Keywords: Polycarboylated oxirane, Polyfunctionalized bromoalkene, Vicinal tricarbonyl compound, α-Bromo ketone, Oxetane intermediate

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(E-pub Ahead of Print)
DOI: 10.2174/1385272823666190112103813
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