Asymmetric Hydrogenation of β-Aryl Alkylidene Malonate Esters: Installing an Ester Group Significantly Increases the Efficiency.

Org Lett

State Key Laboratory and Institute of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.

Published: March 2021

Herein, we report a practical method for efficient asymmetric hydrogenation of β-aryl alkylidene malonates. With a site-specifically tailored chiral spiro iridium catalyst, a series of β-aryl alkylidene malonate esters were hydrogenated to afford chiral malonate esters with good to excellent enantioselectivities (up to 99% ee) and high turnover numbers (up to 19000). The results showed that installing an ester group in α,β-unsaturated carboxylic esters significantly increased the efficiency of their asymmetric hydrogenation reactions.

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http://dx.doi.org/10.1021/acs.orglett.1c00093DOI Listing

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