Enantiodivergent Sulfoxidation Catalyzed by a Photoswitchable Iron Salen Phosphate Complex.

Here we describe a photoswitchable iron(III) salen phosphate catalyst, which is able to catalyze the enantiodivergent oxidation of prochiral aryl alkyl sulfides to chiral aryl alkyl sulfoxides. The stable (S)-axial isomer of the catalyst produced enantioenriched sulfoxides with the (R)-configuration in up to 75 % e.e., whereas the photoisomerized metastable (R)-axial isomer of the catalyst favored the formation of (S)-sulfoxides in up to 43 % e.e. The maximum Δe.e. value obtained in the enantiodivergent sulfoxidation was 118 %, which is identical to the maximum Δe.e. value that was measured in the enantiodivergent epoxidation of alkenes by a related recently described Mn1 catalyst. This iron-based catalyst broadens the scope of photoswitchable enantiodivergent catalysts and may be used in the future to develop a photoswitchable catalytic system that can write digital information on a polymer chain in the form chiral sulfoxide functions. © 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Citation

Pieter J Gilissen, Xiaofei Chen, Joep De Graaf, Paul Tinnemans, Ben L Feringa, Johannes A A W Elemans, Roeland J M Nolte. Enantiodivergent Sulfoxidation Catalyzed by a Photoswitchable Iron Salen Phosphate Complex. Chemistry (Weinheim an der Bergstrasse, Germany). 2023 Apr 25;29(24):e202203539

PMID: 36744844

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