Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine

Shimada, Yasutaka; Usuda, Kazumasa; Okabe, Hirokazu; Suzuki, Tsuguru; Matsumoto, Kazutsugu

doi:10.1016/j.tetasy.2009.11.005

Cited by 16 publications

(8 citation statements)

References 65 publications

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“…Overall, this strategy comprising kinetic resolution and Mitsunobu inversion, can be considered as an EC. Thus, in 2009 the effective preparation of optically active 1,2‐diol monotosylate O ‐acetyl derivatives ( 24 ) was performed using different lipases and polymer‐bound triphenylphosphine for the Mitsunobu reaction (Scheme ) . Lipase PS was able to selectively hydrolyse a set of 2‐acetoxy tosylates in phosphate buffer pH 6.5 at 30 °C containing 10% of diisopropyl ether (DIPE), leading to the ( R )‐alcohols and ( S )‐esters with an excellent enantioselectivities ( E >100).…”

Section: Enzymatic Deracemisation Proceduresmentioning

confidence: 99%

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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 of 1,2‐diol monotosylates derivatives ( 24 ) by the combination of selective lipase‐mediated hydrolysis and the Mitsunobu inversion …”

Section: Enzymatic Deracemisation Proceduresmentioning

confidence: 99%

Deracemisation Processes Employing Organocatalysis and Enzyme Catalysis

et al. 2020

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“…114 An interesting chemoenzymatic enantioconvergent method was reported by Matsumoto and coworkers (Scheme 29). 115,116 Racemic acetate esters were first Scheme 26 Deracemisation of secondary alcohols (using a nonstereoselective ADH) coupled to reductive amination with reductive aminases (e.g., from Aspergillus, AspRedAm). ADHs used in this study were W110A TeSADH and the ADH from Sphingobium yanoikuyae (SyADH).…”

Section: Enantioconvergent Deracemisation Reactionsmentioning

confidence: 99%

“…An interesting chemoenzymatic enantioconvergent method was reported by Matsumoto and coworkers ( Scheme 29 ). 115 , 116 Racemic acetate esters were first submitted to a lipase-mediated KR followed by a chemical Mitsunobu reaction of the resulting alcohol enantiomer yielding essentially enantiomerically pure ( S )-2-acetoxy tosylates. The tedious removal of non-reacted PPh 3 from the Mitsunobu step was circumvented by using insoluble, polymer-supported PPh 3 .…”

Section: Enantioconvergent Deracemisation Reactionsmentioning

confidence: 99%

Synthesis of enantiomerically pure alcohols and amines via biocatalytic deracemisation methods

Musa

Hollmann

Mutti

2019

Catal. Sci. Technol.

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“…In this field, one of the most versatile stereo chemical transformations is the Mitsunobu reaction [22]. It was found that the inversion of the configuration of chiral secondary alcohols following an enzymatic kinetic resolution step was of fruitful application [23,24].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2014

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A series of arylalkylcarbinol derivatives were deracemized through sequential combination of Candida antarctica lipase B (CAL-B) catalyzed resolution by hydrolysis and Mitsunobu stereoinversion. The (S)-acetates were obtained in 71%-99% ee and 76%-89% yields. An enantiocomplementarity was established for the hydrolysis and acylation reactions with CAL-B lipase. Thus, the (S) and (R) enantiomers of Indan-1-yl acetate, 1,2,3,4-tetrahydro-1-naphthalenol acetate and 1-(2-naphthyl) ethyl acetate were obtained in 91%-99% ee and 76%-89% yield.

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Deracemization of 1,2-diol monotosylate derivatives by a combination of enzymatic hydrolysis with the Mitsunobu inversion using polymer-bound triphenylphosphine

Cited by 16 publications

References 65 publications

Deracemisation Processes Employing Organocatalysis and Enzyme Catalysis

Deracemisation Processes Employing Organocatalysis and Enzyme Catalysis

Synthesis of enantiomerically pure alcohols and amines via biocatalytic deracemisation methods

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

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