Development of a One-Pot Tandem Reaction Combining Ruthenium-Catalyzed Alkene Metathesis and Enantioselective Enzymatic Oxidation To Produce Aryl Epoxides

Denard, Carl A.; Bartlett, Mark J.; Wang, Yajie; Lu, Lu; Hartwig, John F.; Zhao, Huimin

doi:10.1021/acscatal.5b00533

Cited by 70 publications

(64 citation statements)

References 40 publications

(37 reference statements)

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“…The intermediately formed ( E )‐stilbene was then epoxidized with high stereoselectivity (up to 94 % ee ). Total turnover numbers exceeding 2,500 demonstrate the high usefulness already on laboratory scale …”

Section: Chemoenzymatic Cascade Reactionsmentioning

confidence: 95%

“…To tal turnover numbers exceeding 2,500 demonstrate the high usefulness already on laboratory scale. [17] Step-wise and concurrent cascades in aqueous systems However,v ery few alternate enzymes offer this stability,w hich limits tandemc atalysis in organic media mostly to lipases. In contrast, operating in aqueous systemsa tn eutral pH allows ah igherf lexibility on the enzyme side.…”

Section: Concurrent Cascades In Organic Mediamentioning

confidence: 99%

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Overcoming the Incompatibility Challenge in Chemoenzymatic and Multi‐Catalytic Cascade Reactions

Schmidt

Castiglione

Kourist

2017

Chemistry A European J

166

118

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Multi-catalytic cascade reactions bear a great potential to minimize downstream and purification steps, leading to a drastic reduction of the produced waste. In many examples, the compatibility of chemo- and biocatalytic steps could be easily achieved. Problems associated with the incompatibility of the catalysts and their reactions, however, are very frequent. Cascade-like reactions can hardly occur in this way. One possible solution to combine, in principle, incompatible chemo- and biocatalytic reactions is the defined control of the microenvironment by compartmentalization or scaffolding. Current methods for the control of the microenvironment of biocatalysts go far beyond classical enzyme immobilization and are thus believed to be very promising tools to overcome incompatibility issues and to facilitate the synthetic application of cascade reactions. In this Minireview, we will summarize recent synthetic examples of (chemo)enzymatic cascade reactions and outline promising methods for their spatial control either by using bio-derived or synthetic systems.

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Section: Chemoenzymatic Cascade Reactionsmentioning

confidence: 95%

Section: Concurrent Cascades In Organic Mediamentioning

confidence: 99%

Overcoming the Incompatibility Challenge in Chemoenzymatic and Multi‐Catalytic Cascade Reactions

Schmidt

Castiglione

Kourist

2017

Chemistry A European J

166

118

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“…The yield of 4 was 1.5 times higher than the hypothetical yield (≤64%) resulting from stepwise reactions. Later, they developed a similar system by using an engineered P450 to convert a mixture of alkenes into a single aryl epoxide in high enantiomeric excess and moderate yield (Scheme 6B) [61].…”

Section: Concurrent Tandem Reactions By Transition-metal Complexes Anmentioning

confidence: 99%

“…GDH, glucose dehydrogenase; NADP, nicotinamide adenine dinucleotide phosphate. Adapted from [61]. Copyright American Chemical Society, 2015.…”

Section: Concurrent Tandem Reactions By Transition-metal Complexes Anmentioning

confidence: 99%

Tandem Reactions Combining Biocatalysts and Chemical Catalysts for Asymmetric Synthesis

Wang

Zhao

2016

Catalysts

Self Cite

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Abstract:The application of biocatalysts in the synthesis of fine chemicals and medicinal compounds has grown significantly in recent years. Particularly, there is a growing interest in the development of one-pot tandem catalytic systems combining the reactivity of a chemical catalyst with the selectivity engendered by the active site of an enzyme. Such tandem catalytic systems can achieve levels of chemo-, regio-, and stereo-selectivities that are unattainable with a small molecule catalyst. In addition, artificial metalloenzymes widen the range of reactivities and catalyzed reactions that are potentially employable. This review highlights some of the recent examples in the past three years that combined transition metal catalysis with enzymatic catalysis. This field is still in its infancy. However, with recent advances in protein engineering, catalyst synthesis, artificial metalloenzymes and supramolecular assembly, there is great potential to develop more sophisticated tandem chemoenzymatic processes for the synthesis of structurally complex chemicals.

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“…As a result, most of these hybrid reactions run sequentially or, alternatively, the catalysts are site‐isolated by compartmentalization or encapsulation techniques ,. Actually, the number of concurrent chemoenzymatic processes with concomitant action of metal and enzyme are still very scarce, and include the pioneering dynamic kinetic resolution (DKR) processes combining a racemizing metal catalyst with an enzymatic transformation, ruthenium‐catalyzed olefin metathesis coupled with monoamine oxidases and P‐450 enzymes,, a simultaneous ruthenium‐catalyzed isomerization of allylic alcohols‐bioreduction, and the oxidation of cyclic amines to lactams by a monoamine oxidase and CuI/H 2 O 2 …”

Section: Introductionmentioning

confidence: 99%

Strengthening the Combination between Enzymes and Metals in Aqueous Medium: Concurrent Ruthenium‐Catalyzed Nitrile Hydration ‐ Asymmetric Ketone Bioreduction

et al. 2018

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A dual ruthenium/ketoreductase catalytic system has been developed for the conversion of β‐ketonitriles into optically active β‐hydroxyamides through an unprecedented hydration/bioreduction cascade process in aqueous medium working in concurrent mode. The ketoreductase‐mediated ketone reduction took place with exquisite stereoselectivity and it was simultaneous to the nitrile hydration promoted by the ruthenium catalyst. The overall transformation occurred: (i) employing commercially and readily available catalytic systems (ii) under mild reaction conditions, (iii) with high degree of conversion and excellent stereoselectivity, and (iv) without the need to isolate intermediates and with high final product yields. This genuine process demonstrates the benefits of combining metal and enzymatic catalysis to tackle the limitations arising from each field.

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Development of a One-Pot Tandem Reaction Combining Ruthenium-Catalyzed Alkene Metathesis and Enantioselective Enzymatic Oxidation To Produce Aryl Epoxides

Cited by 70 publications

References 40 publications

Overcoming the Incompatibility Challenge in Chemoenzymatic and Multi‐Catalytic Cascade Reactions

Overcoming the Incompatibility Challenge in Chemoenzymatic and Multi‐Catalytic Cascade Reactions

Tandem Reactions Combining Biocatalysts and Chemical Catalysts for Asymmetric Synthesis

Strengthening the Combination between Enzymes and Metals in Aqueous Medium: Concurrent Ruthenium‐Catalyzed Nitrile Hydration ‐ Asymmetric Ketone Bioreduction

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