Nanoflow microreactor for dramatic increase not only in reactivity but also in selectivity: Baeyer–Villiger oxidation by aqueous hydrogen peroxide using lowest concentration of a fluorous lanthanide catalyst

Mikami, Kōichi; Yamanaka, Masahiro; Islam, Nazrul; Tonoi, Takayuki; Itoh, Yoshimitsu; Shinoda, Masaki; Kudo, Kenichi

doi:10.1016/j.jfluchem.2006.03.012

Cited by 21 publications

(7 citation statements)

References 55 publications

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“…A number of stereoselective biocatalytic methods have been reported for these lactones, including use of Baeyer–Villiger monooxygenases, alcohol dehydrogenases, and biocatalytic cascades . However, all reported synthetic methods start from functionalized materials, including 11‐hydroxy palmitic acid, coriolic acid, and Massoia lactone …”

Section: Methodsmentioning

confidence: 99%

Regio‐ and Enantio‐selective Chemo‐enzymatic C−H‐Lactonization of Decanoic Acid to (S)‐δ‐Decalactone

et al. 2019

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The conversion of saturated fatty acids to high value chiral hydroxy‐acids and lactones poses a number of synthetic challenges: the activation of unreactive C−H bonds and the need for regio‐ and stereoselectivity. Here the first example of a wild‐type cytochrome P450 monooxygenase (CYP116B46 from Tepidiphilus thermophilus) capable of enantio‐ and regioselective C5 hydroxylation of decanoic acid 1 to (S)‐5‐hydroxydecanoic acid 2 is reported. Subsequent lactonization yields (S)‐δ‐decalactone 3, a high value fragrance compound, with greater than 90 % ee. Docking studies provide a rationale for the high regio‐ and enantioselectivity of the reaction.

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Section: Methodsmentioning

confidence: 99%

Regio‐ and Enantio‐selective Chemo‐enzymatic C−H‐Lactonization of Decanoic Acid to (S)‐δ‐Decalactone

et al. 2019

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“…Changing the reaction media from conventional volatile organic solvents to a form of nonconventional media, with or without chemical manipulation on the catalyst, represents another type of general strategy used to recover and reuse a (chiral) catalyst system . Most frequently, ionic liquids, supercritical fluids (usually supercritical carbon dioxide, SCCO 2 ), , perfluorinated liquids, and even water were utilized as the “green” supplants for those environmentally hazardous organic solvents. Another advantage of the catalysis in such a medium was considered as the easy catalyst separation and recovery under either monophasic or biphasic conditions, with a variable degree of solvent effects on catalytic reactivity and selectivity.…”

Section: Heterogeneous Asymmetric Catalysis In Flowmentioning

confidence: 99%

Recent Advances in Asymmetric Catalysis in Flow

2013

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Asymmetric catalysis in flow has been attracting much attention very recently because of the potential advantages over its batchwise counterpart, such as high-throughput screening and synthesis, easy automation with the integration of on-demand reaction analysis, little or no reaction workup, and potential long-term use of the catalysts in the case of heterogeneous catalysis. Homogeneous asymmetric catalysis performed in a microreactor has demonstrated successful examples in fast catalyst screening, integrated inline/onlineanalysis, microflow photocatalysis, multistep transformation with unstable intermediates, and potential for lower catalyst loading or homogeneous catalyst recylcing. Since heterogeneous asymmetric catalysis serves as a better way than its homogeneous analogue for catalyst separation and recycling, this Review Article summarizes recent development via different catalyst immobilization methods, such as covalent support, a self-supported method, an adsorption method, and H-bonding, electrostatic or ionic interaction, and nonconventional media, as well. In addition, biocatalysis, including enzyme-catalyzed kinetic resolution and transformation, in flow will be discussed either in homogeneous or heterogeneous mode.

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“…The reaction uses hydrogen peroxide as the oxidant in a benzylic hydroperoxide rearrangement reaction (Scheme ). The advantage of using hydrogen peroxide as an oxidizing reagent is low mass transfer limitations in such a liquid–liquid system. − However, it is not uncommon to observe thermal runaway potential for reactions involving organic peroxides or hydrogen peroxide with acids. , The hazard analysis of this chemistry determined that thermal runaway potential exists at ambient conditions. Alternate chemical routes were scouted for the target hydroxypyrrolotriazine 2 , but none proved acceptable.…”

Section: Introductionmentioning

confidence: 99%

Development of a Continuous Plug Flow Process for Preparation of a Key Intermediate for Brivanib Alaninate

LaPorte

Spangler

Hamedi

et al. 2014

Org. Process Res. Dev.

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A thermal runaway potential was identified for the conversion of a tertiary alcohol to a hydroxypyrrolotriazine intermediate in the synthesis of brivanib alaninate. A continuous process was developed to mitigate the potential thermal runaway and allow for safer scale-up. This paper describes the hazard analysis, process development, reactor development, reaction engineering model development, and scale-up of the continuous process. The process includes three separate and stable feed streams that are mixed in distinct order using in-line static mixers. Heat exchangers are arranged and connected to facilitate a "plug flow" reactor scheme allowing sufficient residence time for reaction completion. The process has been scaled-up to the pilot plant and to manufacturing.

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Nanoflow microreactor for dramatic increase not only in reactivity but also in selectivity: Baeyer–Villiger oxidation by aqueous hydrogen peroxide using lowest concentration of a fluorous lanthanide catalyst

Cited by 21 publications

References 55 publications

Regio‐ and Enantio‐selective Chemo‐enzymatic C−H‐Lactonization of Decanoic Acid to (S)‐δ‐Decalactone

Regio‐ and Enantio‐selective Chemo‐enzymatic C−H‐Lactonization of Decanoic Acid to (S)‐δ‐Decalactone

Recent Advances in Asymmetric Catalysis in Flow

Development of a Continuous Plug Flow Process for Preparation of a Key Intermediate for Brivanib Alaninate

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