First dynamic kinetic resolution of selenium-containing chiral amines catalyzed by palladium (Pd/BaSO4) and Candida antartica lipase (CAL-B)

Andrade, Leandro H.; Silva, Alexandre Valotta da; Pedrozo, Eliane C.

doi:10.1016/j.tetlet.2009.05.022

Cited by 52 publications

(11 citation statements)

References 24 publications

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“…Since Reetz and Schimossek [6] reported the use of palladium on charcoal (17) for DKR of amines, several heterogeneous catalysts on varying supporting materials have been introduced for racemization of amines (Table 9). [58][59][60][61][62] The Shvo-type ruthenium complexes 1 [63,64] and the iridium complex 21 [65,66] are unusual examples of homogeneous ones.…”

Section: Racemization Catalysts and Reaction Conditions For Dkr Of Ammentioning

confidence: 99%

Chemoenzymatic Dynamic Kinetic Resolution of Alcohols and Amines

et al. 2010

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Dynamic kinetic resolution (DKR) is an attractive process for the transformation of racemic mixtures into optically active compounds. For successful DKR, efficient racemization is required while the kinetic resolution is proceeding. This Microreview mainly summarizes the recent developments in the DKR of alcohols and amines, based on metal-catalyzed racemization and enzymatic acylation in a single reaction vessel.

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Section: Racemization Catalysts and Reaction Conditions For Dkr Of Ammentioning

confidence: 99%

Chemoenzymatic Dynamic Kinetic Resolution of Alcohols and Amines

et al. 2010

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“…20) (Parvulescu et al, 2009). Pd/BaSO 4 has been employed with immobilized CAL-B at 70°C for DKR of several benzylic amines (Parvulescu et al, 2007(Parvulescu et al, , 2009, including selenium-containing amines (Andrade et al, 2009), with satisfactory yields in 24-72 h, being reused in some cases (Parvulescu et al, 2009). Pd/CaCO 3 has been employed with immobilized CAL-B at 100°C to furnish chiral benzylic amides with high conversions (84-97%) and optical purity (95-98% ee) in less than 2 h by using microwave irradiation (A.…”

Section: Dynamic Kinetic Resolution Of Amines Catalyzed By Lipases Anmentioning

confidence: 99%

Lipases: Valuable catalysts for dynamic kinetic resolutions

Miranda

Souza

2015

Biotechnology Advances

180

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“…Furthermore, the robustness of the chemo-biocatalytic system was proven by the recovery of the catalysts and their reuse in at least 3 reaction cycles without any loss of activity. Recently, Pd/BaSO 4 together with Novozyme 435 was also successfully used for the DKR of selenium-containing chiral amines indicating once more the high versatility of this catalytic system [57].…”

Section: Heterogeneous Catalysts For Racemization and Dkr Of Amines Bmentioning

confidence: 99%

Heterogeneous Catalysts for Racemization and Dynamic Kinetic Resolution of Amines and Secondary Alcohols

et al. 2010

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This paper gives an overview of the available heterogeneous catalysts for racemization of chirally stable secondary alcohols and amines, and of the combination of these catalysts with immobilized enzymes in dynamic kinetic resolution (DKR) for production of enantiopure esters or amides. For the one-pot DKR process, compatibility of enzyme and heterogeneous catalyst is a major issue, and in some cases the combination fails because of (mutual) deactivation. Heterogeneous catalysts of various types, such as zeolites or oxides effect alcohol racemization; they function either via acid catalysis and carbenium chemistry, or via a redox pathway via the ketone. Dynamic kinetic resolution of aliphatic alcohols using a heterogeneous catalyst in mild conditions is however an open challenge. Heterogeneous amine racemization catalysts invariably operate using a redox mechanism via the imine. In this case, the scope encompasses benzylic and aliphatic amines. The practicality of the approach is illustrated with the production of enantiopure N-acylated homoserine lactones, which are signalling compounds in microbial communities.

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First dynamic kinetic resolution of selenium-containing chiral amines catalyzed by palladium (Pd/BaSO4) and Candida antartica lipase (CAL-B)

Cited by 52 publications

References 24 publications

Chemoenzymatic Dynamic Kinetic Resolution of Alcohols and Amines

Chemoenzymatic Dynamic Kinetic Resolution of Alcohols and Amines

Lipases: Valuable catalysts for dynamic kinetic resolutions

Heterogeneous Catalysts for Racemization and Dynamic Kinetic Resolution of Amines and Secondary Alcohols

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