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Abstract <p>The reactions of 1,6-anhydro bridge opening in 1,2-adducts of levoglucosenone with allyl bromide and ethyl ester of α-bromoacetic acid were studied. It was found that the optimal agent for opening the 1,6-anhydro bridge in the allyl derivative adduct is ZnBr<sub>2</sub>–Ac<sub>2</sub>O or ZnСl<sub>2</sub>–Ac<sub>2</sub>O and BF<sub>3</sub>·Et<sub>2</sub>O–Ac<sub>2</sub>O for the Reformatsky adduct. The obtained products of 1,6-anhydro bridge opening in levoglucosenone derivatives are key compounds for the synthesis of carbocycles annulated with a pyran fragment.</p>

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Synthesis and Some Features of 1,6-Anhydro Bridge Opening in 1,2-Adducts of Levoglucosenone

  • 期刊论文

  • 发表日期：

    2025年6月1日

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  • L. Sh. Karamysheva,
  • Yu. A. Khalilova,
  • Sh. M. Salikhov,
  • L. Kh. Fayzullina

摘要

Abstract

The reactions of 1,6-anhydro bridge opening in 1,2-adducts of levoglucosenone with allyl bromide and ethyl ester of α-bromoacetic acid were studied. It was found that the optimal agent for opening the 1,6-anhydro bridge in the allyl derivative adduct is ZnBr2–Ac2O or ZnСl2–Ac2O and BF3·Et2O–Ac2O for the Reformatsky adduct. The obtained products of 1,6-anhydro bridge opening in levoglucosenone derivatives are key compounds for the synthesis of carbocycles annulated with a pyran fragment.