Integrated Cobaloxime and Mesoporous Silica-Supported Ruthenium/Diamine Co-Catalysis for One-Pot Hydration/Reduction Enantioselective Sequential Reaction of Alkynes

Zeyang Liu; Yongjie Wang; Kaihong Liu; Shanshan Wang; Haocheng Liao; Yuanli Zhu; Baoming Hou; Chunxia Tan; Guohua Liu

doi:10.3389/fchem.2021.732542

Integrated Cobaloxime and Mesoporous Silica-Supported Ruthenium/Diamine Co-Catalysis for One-Pot Hydration/Reduction Enantioselective Sequential Reaction of Alkynes

Front Chem. 2021 Sep 22:9:732542. doi: 10.3389/fchem.2021.732542. eCollection 2021.

Authors

Zeyang Liu¹, Yongjie Wang¹, Kaihong Liu¹, Shanshan Wang¹, Haocheng Liao¹, Yuanli Zhu¹, Baoming Hou¹, Chunxia Tan¹, Guohua Liu¹

Affiliation

¹ Key Laboratory of Resource Chemistry of Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, Shanghai Normal University, Shanghai, China.

Abstract

This study developed a cost-efficient hydration/asymmetric transfer hydrogenation (ATH) process for the one-pot synthesis of valuable chiral alcohols from alkynes. During this process, the initial homogeneous cobaloxime-catalyzed hydration of alkynes was followed by heterogeneous Ru/diamine-catalyzed ATH transformation of the in-situ generated ketones, which provided varieties of chiral alcohols in good yields with up to 99% ee values. The immobilized Ru/diamine catalyst could be recycled at least three times before its deactivation in the sequential reaction system. This work shows a general method for developing one-pot asymmetric sequential catalysis towards sustainable organic synthesis.

Keywords: asymmetric catalysis; heterogeneous catalysts; hydration; silica; transfer hydrogenation.