Indium-Mediated Acyloxyallylation-Based Synthesis of Galacto-Configured Higher-Carbon Sugar Alcohols as Potential Phase Change Materials.

ABSTRACT: Sugar alcohols fulfilling specific structural requirements are a substance class with great potential as organic phase change materials (PCMs). Within this work, we demonstrate the indium-mediated acyloxyallylation (IMA) as a useful strategy for the synthesis of higher-carbon sugar alcohols of the galacto-family featuring all hydroxyl groups in a 1,3-anti-relationship with three major synthetic achievements: first, the dihydroxylation of the IMA-derived allylic sugar derivates was systematically studied in terms of diastereoselectivity, revealing a high degree of substrate control toward anti-addition. Second, we demonstrated the use of a "double Mitsunobu" reaction, inverting the stereochemistry of terminal diols. Third, the IMA toolbox was expanded to accomplish the

SUBMITTER: Biedermann N 

PROVIDER: S-EPMC11040715 | biostudies-literature | 2024 Apr

REPOSITORIES: biostudies-literature