Enantiocomplementary Preparation of (S)- and  (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution  and Mitsunobu Inversion: Impact of Lipase Amount

Bouzemi, Nassima; Grib, Ismahane; Houiene, Zahia; Aribi‐Zouioueche, Louisa

doi:10.3390/catal4030215

Cited by 15 publications

(6 citation statements)

References 40 publications

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“…The same procedure was employed by Bouzemi and co‐workers in the deracemisation of a set of arylalkylcarbinol derivatives ( 26 ) employing the lipase B from Candida antarctica (CalB) and the Mitsunobu inversion reaction. CalB was able to catalyse the selective hydrolysis of the racemic starting material to the ( R )‐alcohols and ( S )‐acetates with high selectivity .…”

Section: Enzymatic Deracemisation Proceduresmentioning

confidence: 99%

Deracemisation Processes Employing Organocatalysis and Enzyme Catalysis

et al. 2020

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Deracemisation methods have demonstrated their importance in the preparation of chiral compounds in the last few years. In order to resolve a racemic mixture in a dynamic sense, one enantiomer of the starting material can be converted to the other through a deracemisation procedure, that can be achieved by different mechanisms based on stereoinversion or enantioconvergence, often involving two‐opposite half reactions, with at least one of the reactions being enantioselective enough to finally obtain an enantioenriched chiral compound. The focus of this comprehensive review is on the application of deracemisation procedures in the present century in order to obtain optically active valuable compounds when employing non‐metallic catalysts. Thus, the review will mainly focus on the use of different enzymatic preparations (purified enzymes, cell‐free extracts or whole cell systems) and organocatalysts for the deracemisation of racemic mixtures.

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Section: Enzymatic Deracemisation Proceduresmentioning

confidence: 99%

Deracemisation Processes Employing Organocatalysis and Enzyme Catalysis

et al. 2020

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“…This prompted us to explore the reverse process, ie, lipase-catalysed deacetylation, which is also a well-recognized strategy to get enantio-pure compounds. 69 However, inconsistencies in conversions and enantio-selectivities were observed in the case of reactions in buffer. Subsequently, its enantioselective deacetylation was attempted with various lipases in phosphate buffer (pH 7.0) under ambient condition as per literature protocol.…”

Section: Enantioselective Deacetylation Route Tomentioning

confidence: 99%

“…Subsequently, its enantioselective deacetylation was attempted with various lipases in phosphate buffer (pH 7.0) under ambient condition as per literature protocol. 69 However, inconsistencies in conversions and enantio-selectivities were observed in the case of reactions in buffer. Literature reports also suggested that enzymatic hydrolysis in biphasic/aqueous conditions could pose problems due to difficulty in controlling pH, low solubility of the substrate, etc.…”

Section: Enantioselective Deacetylation Route Tomentioning

confidence: 99%

1‐Hydroxymethyl‐7‐oxabicyclo[2.2.1]hept‐2‐ene skeleton in enantiopure form through enzymatic kinetic resolution

Reddy

Manheri

2019

Chirality

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Lipase-catalysed enantioselective acetylation and deacetylation routes were investigated to prepare 1,5,6-trisubstituted 7-oxabicyclo[2.2.1]hept-2-ene skeleton in enantio-pure form. The racemic alcohol (6) used in acetylation reaction was accessed through Diels-Alder reaction of TBDMS-protected furfuryl alcohol with maleic anhydride, followed by reduction-benzylation-desilylation sequence. After systematic screening of lipases and solvents, Candida antarctica B on acrylic resin in pentane was identified as the best system that gave >98% ee towards the (+) acetate with 40% conversion, in 30 minutes. Absolute stereochemistry of this product was confirmed by X-ray diffraction analysis of its 3,5-dinitrobenzoate derivative (9). Enantioselective deacetylation of the racemic acetate of this starting material was then studied with the same set of lipases. After various optimization studies, Candida antarctica B in toluene as the solvent was found to be the most effective that gave 49% conversion with >99% ee towards the (+)-alcohol (8) at the end of 18 hours.

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“…The complementary process was conducted using CAL-B on the catalyzed acylation of the rac -arylalkylcarbinols, producing the ( S )-alcohols and ( R )-acetates in high enantioselectivities (route b). Subsequently, these mixtures were submitted to a Mitsunobu reaction and provided only the ( R )-acetates (99% ee ( n = 1 or 2)), as seen in Scheme 45 b [ 69 ].…”

Section: Complementary Approaches: Hydrolysis and Esterificationmentioning

confidence: 99%

“… Complementary enzymatic kinetic resolution of rac -arylalkylcarbinyl acetates or rac -arylalkylcarbinols combined with Mitsunobu reaction on the preparation of ( S )- and ( R )-arylalkylcarbinyl acetates via hydrolysis ( a ) or acylation ( b ), respectively [ 69 ]. …”

Section: Complementary Approaches: Hydrolysis and Esterificationmentioning

confidence: 99%

Recent Advances in Lipase-Mediated Preparation of Pharmaceuticals and Their Intermediates

Carvalho

Fonseca

Mattos

et al. 2015

IJMS

123

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Biocatalysis offers an alternative approach to conventional chemical processes for the production of single-isomer chiral drugs. Lipases are one of the most used enzymes in the synthesis of enantiomerically pure intermediates. The use of this type of enzyme is mainly due to the characteristics of their regio-, chemo- and enantioselectivity in the resolution process of racemates, without the use of cofactors. Moreover, this class of enzymes has generally excellent stability in the presence of organic solvents, facilitating the solubility of the organic substrate to be modified. Further improvements and new applications have been achieved in the syntheses of biologically active compounds catalyzed by lipases. This review critically reports and discusses examples from recent literature (2007 to mid-2015), concerning the synthesis of enantiomerically pure active pharmaceutical ingredients (APIs) and their intermediates in which the key step involves the action of a lipase.

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Enantiocomplementary Preparation of (S)- and (R)-Arylalkylcarbinols by Lipase-Catalysed Resolution and Mitsunobu Inversion: Impact of Lipase Amount

Cited by 15 publications

References 40 publications

Deracemisation Processes Employing Organocatalysis and Enzyme Catalysis

Deracemisation Processes Employing Organocatalysis and Enzyme Catalysis

1‐Hydroxymethyl‐7‐oxabicyclo[2.2.1]hept‐2‐ene skeleton in enantiopure form through enzymatic kinetic resolution

Recent Advances in Lipase-Mediated Preparation of Pharmaceuticals and Their Intermediates

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