Cooperative chemoenzymatic and biocatalytic cascades to access chiral sulfur compounds bearing C(sp3)–S stereocentres

Fei Zhao, Ariane Mattana, Ruqaiya Alam, Sarah L. Montgomery, Akash Pandya, Fabrizio Manetti, Beatriz Dominguez () and Daniele Castagnolo ()
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Fei Zhao: University College London
Ariane Mattana: University College London
Ruqaiya Alam: University College London
Sarah L. Montgomery: Johnson Matthey
Akash Pandya: Johnson Matthey
Fabrizio Manetti: University of Siena
Beatriz Dominguez: Johnson Matthey
Daniele Castagnolo: University College London

Nature Communications, 2024, vol. 15, issue 1, 1-13

Abstract: Abstract Biocatalysis has been widely employed for the generation of carbon-carbon/heteroatom stereocentres, yet its application in chiral C(sp3)–S bond construction is rare and limited to enzymatic kinetic resolutions. Herein, we describe the enantioselective construction of chiral C(sp3)–S bonds through ene-reductase biocatalyzed conjugate reduction of prochiral vinyl sulfides. A series of cooperative sequential/concurrent chemoenzymatic and biocatalytic cascades have been developed to access a broad range of chiral sulfides, including valuable β-hydroxysulfides bearing two adjacent C(sp3)–S and C(sp3)–O stereocentres, in a stereoconvergent manner with good to excellent yields (up to 96%) and enantioselectivities (up to >99% ee). Notably, this biocatalytic strategy allows to overcome the long-standing shortcomings of catalyst poisoning and C(sp2)/C(sp3)–S bond cleavage faced in transition-metal-catalyzed hydrogenation of vinyl sulfides. Finally, the potential of this methodology is also exemplified by its broader application in the stereoconvergent assembly of chiral C(sp3)–N/O/Se bonds with good to excellent enantioselctivities.

Date: 2024
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DOI: 10.1038/s41467-024-52608-8

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