Mild dynamic kinetic resolution of amines by coupled visible-light photoredox and enzyme catalysis

Yang, Qing; Zhao, Fang; Zhang, Na; Liu, Mingke; Hu, Huanhuan; Zhang, Jingjie; Zhou, Shaolin

doi:10.1039/c8cc07990k

Cited by 29 publications

(26 citation statements)

References 84 publications

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“…photoredox catalysis [175]. They then combined this with an enzyme-mediated acylation to achieve a DKR of primary amines using Novozym 435 (Scheme 77).…”

Section: Enzyme Catalysismentioning

confidence: 99%

Recent developments in enantioselective photocatalysis

Prentice¹,

Morrisson²,

Smith³

et al. 2020

Beilstein J. Org. Chem.

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Enantioselective photocatalysis has rapidly grown into a powerful tool for synthetic chemists. This review describes the various strategies for creating enantioenriched products through merging enantioselective catalysis and photocatalysis, with a focus on the most recent developments and a particular interest in the proposed mechanisms for each. With the aim of understanding the scope of each strategy, to help guide and inspire further innovation in this field.

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“…photoredox catalysis [175]. They then combined this with an enzyme-mediated acylation to achieve a DKR of primary amines using Novozym 435 (Scheme 77).…”

Section: Enzyme Catalysismentioning

confidence: 99%

Recent developments in enantioselective photocatalysis

Prentice¹,

Morrisson²,

Smith³

et al. 2020

Beilstein J. Org. Chem.

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“…Another example of a cooperative photo‐biocatalytic approach was reported by Zhou and co‐workers (Scheme ) . Although enzymatic kinetic resolution results in a maximum yield of 50 %, DKR enables full conversion to the enantiopure product through racemization of the undesired enantiomeric product in situ.…”

Section: Photo‐biocatalysis By Application Of Isolated Enzymes or Celmentioning

confidence: 99%

“…Another example of ac ooperative photo-biocatalytic approach was reported by Zhou and co-workers (Scheme 17). [73] Althoughe nzymatic kinetic resolution results in am aximum yield of 50 %, DKR enables full conversion to the enantiopure product throughr acemization of the undesired enantiomeric T he photoexcited Ir III *c atalyst is reduced by the thiol n-OctSHt op roduce Ir II and at hiyl radical, which abstracts a hydrogen radical from 84.T he subsequently formed a-amino radicalintermediate undergoes areversehydrogen atom transfer (HAT) from n-OctSH to afford rac-84,w hile the thiyl radical oxidizesIr II and regenerates the ground state of the photocatalyst. The photocatalyst, enzyme, and HATc atalyst showed good compatibility, thus facilitating ac ooperative reaction system.T he investigated substrate scope included both aryl and long-and short-chain alkyl groups.…”

Section: Decarboxylation Of Fatty Acidsmentioning

confidence: 99%

Biocatalysis Fueled by Light: On the Versatile Combination of Photocatalysis and Enzymes

Seel

Gulder

2019

ChemBioChem

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Enzymes catalyze a plethora of highly specific transformations under mild and environmentally benign reaction conditions. Their fascinating performances attest to high synthetic potential that is often hampered by operational obstacles such as in vitro cofactor supply and regeneration. Exploiting light and combining it with biocatalysis not only helps in overcoming these drawbacks, but the fruitful liaison of these two fields of “green chemistry” also offers opportunities to unlock new synthetic reactivities. In this review we provide an overview of the wide variety of photo‐biocatalysis, ranging from the photochemical delivery of electrons required in redox biocatalysis and photochemical cofactor and reagent (re)generation to direct photoactivation of enzymes enabling reactions unknown in nature. We highlight synthetically relevant transformations such as asymmetric reactions facilitated by the combination of light as energy source and enzymes’ catalytic power.

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“…Photochemical amine racemization via α‐amino alkyl radical intermediates coupled to enantioselective enzymatic acylation for the dynamic kinetic resolution of amines …”

Section: Combined Enzyme and Photoredox Catalysis In Cascade Reactmentioning

confidence: 99%

Reductive Amination and Enantioselective Amine Synthesis by Photoredox Catalysis

et al. 2019

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Photochemistry usually functions on a one‐photon‐one‐electron basis, leading to unstable radical intermediates that must be intercepted rapidly to allow efficient product formation. This can render multi‐electron reductions and enantioselective reactions particularly challenging. In this minireview, we discuss recent advances in the area of photo‐driven multi‐electron transfer with a particular focus on our own work on reductive amination and the enantioselective synthesis of amines by combined photoredox and enzyme catalysis. Polarity‐matched hydrogen atom transfer (HAT) between photochemically‐generated α‐amino alkyl radicals and thiols is a key step in these reactions. A cyclic reaction network comprised of light‐driven imine reduction by an Ir‐photocatalyst and enantioselective amine oxidation by the enzyme monoamine oxidase (MAO‐N‐9) was used to obtain enantioenriched amines from imines.

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Mild dynamic kinetic resolution of amines by coupled visible-light photoredox and enzyme catalysis

Abstract: A mild and efficient dynamic kinetic resolution (DKR) of amines was achieved by combining visible-light-induced photoredox catalysis and enzyme catalysis. This dual catalytic system was appropriate for both monoamines and 1,4-diamines.

Cited by 29 publications

References 84 publications

Recent developments in enantioselective photocatalysis

Recent developments in enantioselective photocatalysis

Biocatalysis Fueled by Light: On the Versatile Combination of Photocatalysis and Enzymes

Reductive Amination and Enantioselective Amine Synthesis by Photoredox Catalysis

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