Combination of gold and redox enzyme catalysis to access valuable enantioenriched aliphatic β-chlorohydrins

Escot, Lorena; González‐Granda, Sergio; Gotor‐Fernández, Vicente; Lavandera, Iván

doi:10.1039/d2ob01953a

Cited by 8 publications

(3 citation statements)

References 48 publications

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“…A scalable, enantioselective synthesis of β-chlorohydrins has been developed by combining gold and enzymatic catalysis (Scheme 3). 32 The one-pot process involved gold( i )-catalysed hydration of chloroalkynes, followed by asymmetric reduction of the resulting α-chloroketone with an alcohol dehydrogenase (ADH). The general strategy showed good scope for aliphatic chloroalkynes and produced the β-chlorohydrins in high yields and excellent enantioselectivities.…”

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Sutherland

2023

Nat. Prod. Rep.

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Sutherland

2023

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“…This improved the synthetic applicability of the process, avoiding the formation of a by‐product coming from the addition of 2‐PrOH to the alkyne moiety. In addition, this method has also been recently extended to aliphatic substrates (Scheme 9B) [46] …”

Section: Metal‐enzyme Cascade Processesmentioning

confidence: 99%

“…In addition, this method has also been recently extended to aliphatic substrates (Scheme 9B). [46] Rueping and co-workers have described a sequential process to obtain chiral amines in this case (Scheme 9C). [47] AuCl in low loading was used for the hydration of different aromatic alkynes combined with a biotransamination.…”

Section: Alkyne Hydrationmentioning

confidence: 99%

Chemoenzymatic Cascades Combining Biocatalysis and Transition Metal Catalysis for Asymmetric Synthesis

et al. 2023

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The combination of catalytic methods provides multiple advantages in organic synthesis, allowing access to diverse organic molecules in a straightforward manner. Merging metal and enzyme catalysis is currently receiving great attention due to the possibility to assemble metal catalysis in C−C coupling, olefin metathesis, hydration and other reactions with the exquisite stereospecificity displayed by enzymes. Thus, this minireview is organized based on the action of the metal species (Pd, Ru, Au, Ir, Fe…) in combination with different enzymes. Special attention will be paid to the design of sequential processes and concurrent cascades, presenting solutions such as the use of surfactants or compartmentalization strategies for those cases where incompatibilities could hamper the overall process.

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Gold and Biocatalysis for the Stereodivergent Synthesis of Nor(pseudo)ephedrine Derivatives: Cascade Design Toward Amino Alcohols, Diols, and Diamines

et al. 2023

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The combination of gold(I) and enzyme catalysis has provided access to a series of nor(pseudo)ephedrine derivatives in a regio‐ and stereoselective manner. The approach involves developing IPrAuNTf2‐catalyzed hydration of 1‐phenylprop‐2‐yn‐1‐yl acetate or N‐(1‐phenylprop‐2‐yn‐1‐yl)acetamide, followed by (dynamic) asymmetric biotransamination or bioreduction of the corresponding keto ester or keto amide intermediates. Enzyme actions were completely selective towards the modification of the methyl ketones in a highly stereoselective manner, allowing the synthesis of enantio‐ and diastereomerically enriched products using either racemic or optically active starting materials. Thus, a series of amino alcohol, diol, and diamine derivatives were produced from propargyl esters or amides (57 to 86% isolated yield), the biocatalyst of choice determining the (stereo)selectivity of the overall cascade process (70–99% diastereomeric excess and >98% enantiomeric excess), and providing access to nor(pseudo)ephedrine compounds in a straightforward manner.

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Combination of gold and redox enzyme catalysis to access valuable enantioenriched aliphatic β-chlorohydrins

Abstract: The synthesis of enantioenriched β-chlorohydrins is highly appealing due to their relevance as building-blocks in organic synthesis. However, the approximation to aliphatic derivatives is particularly challenging due to the difficulties...

Cited by 8 publications

References 48 publications

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Chemoenzymatic Cascades Combining Biocatalysis and Transition Metal Catalysis for Asymmetric Synthesis

Gold and Biocatalysis for the Stereodivergent Synthesis of Nor(pseudo)ephedrine Derivatives: Cascade Design Toward Amino Alcohols, Diols, and Diamines

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