Biocatalytic approaches towards the stereoselective synthesis of vicinal amino alcohols

Gupta, Pankaj; Mahajan, Neha

doi:10.1039/c8nj00485d

Cited by 72 publications

(43 citation statements)

References 227 publications

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“…The vicinal amino alcohol moiety is a wide spread structural motif in large number of biologically active molecules (natural as well as synthetic) such as β‐blockers, antibiotics, and other enzyme inhibitors 59–61 . These can also be used as chiral catalysts or ligands in a variety of asymmetric synthesis, such as stereoselective dialkylzinc addition to aldehydes, 62 Henry reactions, 63 and pericyclic reactions 64,65 .…”

Section: Applicationsmentioning

confidence: 99%

A review on Arthrobacter sp. lipase: A versatile biocatalyst for the kinetic resolution to access enantiomerically pure/enriched compounds

et al. 2021

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Over the last few years, there has been a dramatic increase in the number of reports related to Arthrobacter sp. lipase (ABL:MTCC No. 5125) catalyzed kinetic resolution performed in biphasic media. A strain displaying esterase/lipase activity and designated as ABL was isolated, during the course of a screening program at Indian Institute of Integrative Medicine, Jammu. Considerable research has shown that reactions catalyzed by ABL are more selective than many commercial lipases. Since new applications of this lipase are emerging, there is a great need to provide all the relevant information exclusively. This review article is an attempt to cover all the relevant reports based on isolation, purification, immobilization, and application of ABL in the biopharmaceutical sector.

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Section: Applicationsmentioning

confidence: 99%

A review on Arthrobacter sp. lipase: A versatile biocatalyst for the kinetic resolution to access enantiomerically pure/enriched compounds

et al. 2021

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“…[2] Consequently,t he asymmetric synthesis of enantioenriched b-amino alcohols,p articularly via asymmetric catalytic reactions,h as drawn considerable attentions. [3] Despite the fact that as eries of elegant methods have been developed for asymmetric synthesis of b-amino alcohols, [4] methods that can generate chiral b-amino tertiary alcohols are still limited. [5] Kinetic resolution (KR) is one of the most reliable and practical methods to produce enantioenriched alcohols in both academia and industry,a nd al arge number of elegant biocatalytic and nonenzymatic methods have been developed to date.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Enamide–Imine Tautomerism in the Kinetic Resolution of Tertiary Alcohols

Tang

et al. 2021

Angewandte Chemie

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An efficient protocol for kinetic resolution of tertiary alcohols has been developed through an unprecedented asymmetric enamide-imine tautomerism process enabled by chiral phosphoric acid catalysis.Abroad range of racemic 2arylsulfonamido tertiary allyl alcohols could be kinetically resolved with excellent kinetic resolution performances (with sfactor up to > 200). This method is particularly effective for as eries of 1,1-dialkyl substituted allyl alcohols,w hichp roduced chiral tertiary alcohols that would be difficult to access via other asymmetric methods.F acile and versatile transformations of the chiral a-hydroxy imine and enamide products,e specially the efficient stereodivergent synthesis of all four stereoisomers of b-amino tertiary alcohols using one enantiomer of the catalyst, demonstrated the value of this kinetic resolution method.

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“…Compounds containing an azido group have a particular synthetic importance, and they caught the attention of organic chemists already in the previous century. They are key intermediates for the synthesis of aminoalcohols [4][5][6], lactams [7], amino sugars [8], oxazolines [9], and are important in the synthesis of carbohydrates and nucleosides [10,11].…”

Section: Introductionmentioning

confidence: 99%

Two (Chemo)-Enzymatic Cascades for the Production of Opposite Enantiomers of Chiral Azidoalcohols

Calderini

Süss²,

Hollmann

et al. 2021

Catalysts

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Multi-step cascade reactions have gained increasing attention in the biocatalysis field in recent years. In particular, multi-enzymatic cascades can achieve high molecular complexity without workup of reaction intermediates thanks to the enzymes’ intrinsic selectivity; and where enzymes fall short, organo- or metal catalysts can further expand the range of possible synthetic routes. Here, we present two enantiocomplementary (chemo)-enzymatic cascades composed of either a styrene monooxygenase (StyAB) or the Shi epoxidation catalyst for enantioselective alkene epoxidation in the first step, coupled with a halohydrin dehalogenase (HHDH)-catalysed regioselective epoxide ring opening in the second step for the synthesis of chiral aliphatic non-terminal azidoalcohols. Through the controlled formation of two new stereocenters, corresponding azidoalcohol products could be obtained with high regioselectivity and excellent enantioselectivity (99% ee) in the StyAB-HHDH cascade, while product enantiomeric excesses in the Shi-HHDH cascade ranged between 56 and 61%.

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Biocatalytic approaches towards the stereoselective synthesis of vicinal amino alcohols

Abstract: The global need for clean manufacturing technologies and the management of hazardous chemicals and waste present new research challenges to both chemistry and biotechnology.

Cited by 72 publications

References 227 publications

A review on Arthrobacter sp. lipase: A versatile biocatalyst for the kinetic resolution to access enantiomerically pure/enriched compounds

A review on Arthrobacter sp. lipase: A versatile biocatalyst for the kinetic resolution to access enantiomerically pure/enriched compounds

Asymmetric Enamide–Imine Tautomerism in the Kinetic Resolution of Tertiary Alcohols

Two (Chemo)-Enzymatic Cascades for the Production of Opposite Enantiomers of Chiral Azidoalcohols

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