Selective and Scalable Synthesis of Sugar Alcohols by Homogeneous Asymmetric Hydrogenation of Unprotected Ketoses.

Selective and Scalable Synthesis of Sugar Alcohols by Homogeneous Asymmetric Hydrogenation of Unprotected Ketoses.
Angew Chem Int Ed Engl. 2020 Sep 14;:
Authors: Tindall DJ, Mader S, Kindler A, Rominger F, Hashmi ASK, Schaub T
Abstract
Sugar alcohols are of great importance to the food industry and are promising building blocks for bio-based polymers. Industrially, they are produced by heterogeneous hydrogenation of sugars with H 2 , usually with none to low stereoselectivities . Now, we present a homogeneous system based on commercially available components (DTBM-SEGPHOS and [RuCl 2 (benzene)] 2 ), which not just increases the overall yield (d.r. up to 31:1), but also allows a wide range of unprotected, densely functionalized ketoses to be diastereoselectively hydrogenated by choosing the appropriate ligand configuration. Furthermore, the system proves to be reliable on a multi-gram scale allowing sugar alcohols to be isolated in large quantities at high atom economy.
PMID: 32926512 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - September 13, 2020 Category: Chemistry Authors: Tindall DJ, Mader S, Kindler A, Rominger F, Hashmi ASK, Schaub T Tags: Angew Chem Int Ed Engl Source Type: research