Mechanistic Complexity of Asymmetric Transfer Hydrogenation with Simple Mn-Diamine Catalysts

Robbert Van Putten, Georgy A. Filonenko, Angela Gonzalez De Castro, Chong Liu, Manuela Weber, Christian Müller, Laurent Lefort, Evgeny Pidko

Research output: Contribution to journalArticleScientificpeer-review

7 Citations (Scopus)
54 Downloads (Pure)

Abstract

The catalytic asymmetric transfer hydrogenation (ATH) of ketones is a powerful methodology for the practical and efficient installation of chiral centers. Herein, we describe the synthesis, characterization, and catalytic application of a series of manganese complexes bearing simple chiral diamine ligands. We performed an extensive experimental and computational mechanistic study and present the first detailed experimental kinetic study of Mn-catalyzed ATH. We demonstrate that conventional mechanistic approaches toward catalyst optimization fail and how apparently different precatalysts lead to identical intermediates and thus catalytic performance. Ultimately, the Mn-N,N complexes under study enable quantitative ATH of acetophenones to the corresponding chiral alcohols with 75-87% ee.

Original languageEnglish
Pages (from-to)3187-3196
Number of pages10
JournalOrganometallics
Volume38
Issue number16
DOIs
Publication statusPublished - 2019

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