Stereoselective Enzymatic Acylations (Transesterifications)

Chênevert, Robert; Pelchat, Nicholas; Jacques, Frédéric

doi:10.2174/138527206777698093

Cited by 45 publications

(7 citation statements)

References 174 publications

(187 reference statements)

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“…[17][18][19] Following this publication, numerous reports of the enantioselective lipase-mediated acylation of amines appeared in the 1990s and the field has since gained significant industrial academic and significance, as described in a number of recent reviews. [20][21][22][23][24][25][26][27][28][29] Herein we report the highly enantioselective CALB/Novozym 435-and amano lipase PS-catalyzed acylation of 1-(3 0 -bromophenyl)ethylamine (RS)-1 with ethyl 2-methoxyacetate as the acyl donor, to furnish the (S)-amine (S)-1 and (R)-2 00 -methoxyacetamide (R)-2 in high yield (90-96%) and high enantiopurity (ee >99%). The enantiomers of 1 and 2 were required with enantiopurities >99.5% as intermediates in the synthesis of IB kinase (IKK) modulators and other pharmaceuticals.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective enzymatic acylation of 1-(3′-bromophenyl)ethylamine

Gill

Das

Patel

2007

Tetrahedron: Asymmetry

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Section: Introductionmentioning

confidence: 99%

Enantioselective enzymatic acylation of 1-(3′-bromophenyl)ethylamine

Gill

Das

Patel

2007

Tetrahedron: Asymmetry

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“…With the aim to fill this gap, this contribution offers a guide to the choice of the most suitable acyl donors for esterification reactions for both the laboratory and industrial scale. The synthesis and applications of these acyl donors have already been described in some excellent reviews, [9][10][11] to which the reader is referred. Here, the greenness of the most used of them (Table 1) is assessed in comparison with the baseline case, i.e.…”

Section: What Is Green About Biocatalysis?mentioning

confidence: 99%

Enzymatic acylation: assessing the greenness of different acyl donors

Paravidino

Hanefeld

2011

Green Chem.

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The hydrolase-catalyzed esterification of alcohols is the best established enzymatic transformation in today's organic chemistry, along with the corresponding ester hydrolysis. Over the years, various different acyl donors have been proposed to overcome the major limitation of the condensation of an alcohol and an acid, the unfavourable equilibrium. This review aims at screening the actual number of applications of the different acyl donors, and at assessing the "greenness" (or lack thereof) of the most applied among them. Indeed, the use of an enzyme to catalyze an esterification is often regarded as sufficient to define the whole transformation as "green". However, this definition can easily be misinterpreted if the contribution of the acyl donor to the overall process is overlooked, as is often the case. Aiming at filling this gap, this contribution evaluates the advantages and disadvantages of the acyl donors, and assesses their green credentials using an efficient tool in strategic planning, a strengths-weaknessesopportunities-threats (SWOT) analysis. A calculation of the atom economy and E-factor for representative acylations involving each donor is included, as well as an analysis of the adherence of each process to the twelve principles of Green Chemistry.

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“…To this end, lipases have been successfully employed to catalyze the stereoselective hydrolysis or acylation of racemic starting materials, in order to accomplish the asymmetric synthesis of chiral building blocks. Since the stereoisomeric forms of a given compound usually show different biological activities, the industrial production of a number of active pharmaceutical ingredients (APIs), flavors, fragrances, natural products, and other bioactive chemicals [4][5][6][7][8][9][10][11][12] looks toward their stereoselective synthesis. In this context, the 'green' biocatalytic processes, and especially the approaches involving lipase-mediated resolution steps, have gained increasing relevance in the last forty years [13].…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Synthesis of Terpenoids through Lipase-Mediated Resolution Approaches

Serra¹,

Simeis²

2020

Catalysts

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This review article focuses on the scientific developments concerning the lipase-mediated synthesis of terpenoids that have been reported in the literature during the last twenty years. More specifically, this review describes in depth the resolution approaches that allow the preparation of the chiral building blocks used for the stereoselective synthesis of bioactive terpenoids. The synthetic methods that have given new and innovative perspectives from a scientific standpoint, and the preparative approaches that possess industrial importance, are described thoroughly.

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Stereoselective Enzymatic Acylations (Transesterifications)

Cited by 45 publications

References 174 publications

Enantioselective enzymatic acylation of 1-(3′-bromophenyl)ethylamine

Enantioselective enzymatic acylation of 1-(3′-bromophenyl)ethylamine

Enzymatic acylation: assessing the greenness of different acyl donors

Stereoselective Synthesis of Terpenoids through Lipase-Mediated Resolution Approaches

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