2016
DOI: 10.1021/acscatal.6b01031
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Integrated Heterogeneous Metal/Enzymatic Multiple Relay Catalysis for Eco-Friendly and Asymmetric Synthesis

Abstract: Organic synthesis is in general performed using stepwise transformations where isolation and purification of key intermediates is often required prior to further reactions. Herein we disclose the concept of integrated heterogeneous metal/enzymatic multiple relay catalysis for eco-friendly and asymmetric synthesis of valuable molecules (e.g., amines and amides) in one-pot using a combination of heterogeneous metal and enzyme catalysts. Here reagents, catalysts, and different conditions can be introduced through… Show more

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Cited by 49 publications
(40 citation statements)
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“…Córdova and co-workers disclosed asymmetric one-pot heterogeneous metal -enzymatic relay catalytic processes using Pd NPs anchored on aminopropyl-functionalized mesocellular silica foam catalyst developed previously (Pd NPs/ support, 97 Scheme 3). 223 Aromatic ketones 180 were transformed into racemic amines 181 by reductive amination using HCOONH 4 for the in situ generation of imines and also the hydrogen source in the reductive step catalysed by Pd. The enzymatic KR of the racemic amines followed this heterogeneous catalytic step by transformation of 181 into amides 182 using lipase (CALB, Novozym-435) catalyst and ethyl methoxyacetate as acylation agent.…”
Section: View Article Onlinementioning
confidence: 99%
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“…Córdova and co-workers disclosed asymmetric one-pot heterogeneous metal -enzymatic relay catalytic processes using Pd NPs anchored on aminopropyl-functionalized mesocellular silica foam catalyst developed previously (Pd NPs/ support, 97 Scheme 3). 223 Aromatic ketones 180 were transformed into racemic amines 181 by reductive amination using HCOONH 4 for the in situ generation of imines and also the hydrogen source in the reductive step catalysed by Pd. The enzymatic KR of the racemic amines followed this heterogeneous catalytic step by transformation of 181 into amides 182 using lipase (CALB, Novozym-435) catalyst and ethyl methoxyacetate as acylation agent.…”
Section: View Article Onlinementioning
confidence: 99%
“…223 Palladium NPs stabilized by thermostable protein (Pd NPs/Te-Dps; Dps: DNA binding protein from starved cells) was used in the one-pot sequential Suzuki-Miyaura crosscoupling and enzymatic enantioselective reduction of phenylboronic acid 39 and phenyl iodide 183 derivatives, with one of the substrates bearing the acetyl group in the para position. The acetyl biaryl intermediates 184 were reduced to chiral biaryl alcohols 40.…”
Section: View Article Onlinementioning
confidence: 99%
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“…Most recently, Berglund and co-workers integrated heterogeneous Pd(0)-aminopropyl-mesocellular foam (Pd(0)-AmP-MCF) or Pd(0)-aminopropyl-conrolled pore glass (Pd(0)-AmP-CPG) and CALB catalysts in one-pot for eco-friendly and asymmetric synthesis of valuable molecules such as amines and amides from an aldehyde, ketone or an alcohol respectively in good to high overall yields [50]. In this work, they developed several novel cocatalytic relay sequences, including reductive amination/amidation (Scheme 5A), aerobic oxidation/reductive amination/amidation (Scheme 5B), and reductive amination/dynamic kinetic resolution (Scheme 5C).…”
Section: Other Tandem Reactions By Transition Metal Catalysts and Lipmentioning
confidence: 99%
“…All of these features characterize a sustainable and eco-friendly technology. Based on the above challenges and our previous experience in developing palladium based heterogenous catalysts for various green chemical transformations [23][24][25][26][27][28][29] , we designed an eco-friendly approach for the preparation of heterogeneous and multifunctional palladium catalysts suitable for a wide spectrum of chemical transformations. The activity and versatility of the designed catalysts was demonstrated in the Suzuki-Miyaura cross-coupling reaction, aerobic oxidation approach of allylic alcohols and stereoselective cascade carbocyclization reactions (Fig.…”
mentioning
confidence: 99%