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1.0 Introduction

DOI: 10.1055/sos-SD-226-00001

de Vries, J. G.Science of Synthesis: Catalytic Reduction in Organic Synthesis, (201711.

I have been somehow engaged with reduction reactions my entire working life. My doctoral thesis was on chiral NADH models that were used for asymmetric reduction of activated ketones, and, in passing, I also invented the reduction of aldehydes and ketones using sodium dithionite. None of this was catalytic, of course. From my six years as a medicinal chemist in the pharma industry, I particularly remember the hydrogenolysis of para-nitrobenzyl esters as the last step in a lengthy total synthesis of carbapenems, and later the hydrogenolysis of the benzyloxycarbonyl protecting groups of peptides that were going to be the ultimate painkillers. When I moved to DSM I was encouraged to work on asymmetric hydrogenation. Initially, we developed a water-soluble rhodium–bisphosphine catalyst for asymmetric imine hydrogenation that was highly enantioselective, but too expensive. Thus, after I became part-time professor in Groningen, together with Adri Minnaard and Ben Feringa, we focused on the development of cheap and simple ligands, an endeavor that culminated in the invention of the monodentate phosphoramidite ligands for the rhodium-, iridium-, and ruthenium-catalyzed homogeneous hydrogenation of a range of different substrates. At DSM, together with Laurent Lefort, we managed to robotize the ligand synthesis, allowing us to make and screen 96 ligands in two days. This eventually also led to a large-scale asymmetric hydrogenation process. In my current research, here at the Leibniz-Institut für Katalyse in Rostock, I also use hydrogenation and hydrogenolysis extensively for the deoxygenation of biomass and biomass-derived platform chemicals.

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