Transformation of Sugars into Chiral Polyols over a Heterogeneous Catalyst

Masazumi Tamura, Naoto Yuasa, Ji Cao, Yoshinao Nakagawa, Keiichi Tomishige

Research output: Contribution to journalArticlepeer-review

31 Citations (Scopus)

Abstract

Transformation of sugars, while maintaining the intrinsic stereochemical structure, is desirable. However, such a transformation requires multistep synthesis with protection and deprotection of the OH groups. Herein, a new method for selective transformation of sugar derivatives into chiral building blocks and a diol synthon, with retention of the intrinsic configuration (stereo- and regioselectively), is demonstrated. The method is based on the selective recognition of cis-vicinal OH groups in sugars and leads to the one-pot removal of the cis-vicinal OH groups, without protection of OH groups (except the OH group of the hemiacetal group), over a heterogeneous CeO2-supported ReOx and Pd (ReOx-Pd/CeO2) catalyst by using H2 as a reducing agent.

Original languageEnglish
Pages (from-to)8058-8062
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number27
DOIs
Publication statusPublished - 2018 Jul 2

Keywords

  • carbohydrates
  • cerium oxide
  • heterogeneous catalysis
  • hydrogenation
  • rhenium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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