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Manganese‐Catalyzed anti ‐Selective Asymmetric Hydrogenation of α‐Substituted β‐Ketoamides
Author(s) -
Zhang Linli,
Wang Zheng,
Han Zhaobin,
Ding Kuiling
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202006383
Subject(s) - enantioselective synthesis , stereoselectivity , manganese , kinetic resolution , selectivity , chemistry , catalysis , combinatorial chemistry , molecule , asymmetric hydrogenation , stereoisomerism , organic chemistry
A Mn‐catalyzed diastereo‐ and enantioselective hydrogenation of α‐substituted β‐ketoamides has been realized for the first time under dynamic kinetic resolution conditions. anti ‐α‐Substituted β‐hydroxy amides, which are useful building blocks for the synthesis of bioactive molecules and chiral drugs, were prepared in high yields with excellent selectivity (up to >99 % dr and >99 % ee ) and unprecedentedly high activity (TON up to 10000). The origin of the excellent stereoselectivity was clarified by DFT calculations.