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Synfacts 2022; 18(05): 0529
DOI: 10.1055/s-0041-1737423
Polymer-Supported Synthesis

Catalytic Hydration/Enantioselective Reductive Amination Cascade Reaction of Propargyl Ethers

Contributor(s):
Yasuhiro Uozumi
,
Teruki Takahashi
Chang F, Wang C, Chen Q, Zhang Y, Liu G. * Shanghai Normal University, P. R. of China
A Chemoenzymatic Cascade Combining a Hydration Catalyst with an Amine Dehydrogenase: Synthesis of Chiral Amines.

Angew. Chem. Int. Ed. 2022;
61: e202114809
DOI: 10.1002/anie.202114809.
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Key words

asymmetric catalysis - hydration - reductive amination - amine dehydrogenase - propargyl ethers

Significance

An Au/carbene complex was encapsulated within the cavities of hollow-shell mesoporous silica nanoparticles to form catalyst 1 (eq. 1). By using a combination of catalyst 1 and the amine dehydrogenase GkAmDH, a hydration/enantioselective reductive amination cascade reaction of propargyl ethers was promoted in the presence of nicotinamide adenine dinucleotide (NAD+) and formate dehydrogenase (FDH) to give the corresponding chiral amines in ≤98% yield and 99% ee (eq. 2).


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Comment

Catalyst 1 promoted the hydration of phenyl propargyl ether to give phenoxyacetone. GkAmDH then catalyzed the enantioselective reductive amination of phenoxyacetone. The cascade reaction using the homogeneous Au/carbene complex IPrAuOTf with GkAmDH did not give the desired amines, due to deactivation of GkAmDH. The hollow-shell silica of catalyst 1 prevents interaction with the Au/carbene complex so that GkAmDH retains its catalytic properties to complete the chemoenzymatic cascade.


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Publication History

Article published online:
20 April 2022

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