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

Angewandte Chemie (International ed. in English) (2020-09-15)
Daniel J Tindall, Steffen Mader, Alois Kindler, Frank Rominger, A Stephen K Hashmi, Thomas Schaub
RÉSUMÉ

Sugar alcohols are of great importance for the food industry and are promising building blocks for bio-based polymers. Industrially, they are produced by heterogeneous hydrogenation of sugars with H2 , usually with none to low stereoselectivities. Now, we present a homogeneous system based on commercially available components, which not only increases the overall yield, but also allows a wide range of unprotected ketoses to be diastereoselectively hydrogenated. Furthermore, the system is reliable on a multi-gram scale allowing sugar alcohols to be isolated in large quantities at high atom economy.

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Ru(OAc)2[(R)-dtbm-SEGPHOS®], Takasago