Application of hydrolytic kinetic resolution (HKR) in the synthesis of bioactive compounds

Kumar, Pradeep; Naidu, Vasudeva; Gupta, Priti

doi:10.1016/j.tet.2006.12.015

Cited by 91 publications

(24 citation statements)

References 209 publications

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“…A platinum catalyst reported by Strukul and co-workers has been applied to the epoxidization of several terminal olefins with medium to good enantioselective (58-83% ee) with H 2 O 2 as the terminal oxidant in CH 2 Cl 2 [123]. Recently, the di--oxo Ti-salalen complex (8) has been used for the epoxidation of some terminal aliphatic alkenes in CH 2 Cl 2 with aqueous hydrogen peroxide as the oxidant, affording chiral oxides with good enantioselectivity (79-97% ee) (Scheme 10a) [118].…”

Section: Classic Methods For the Asymmetric Epoxidation Of Terminal Amentioning

confidence: 99%

“…There are two major approaches to chiral epoxide formation: the direct stereospecific epoxidation of alkenes and the resolution of racemates, such as the hydrolytic kinetic resolution (HKR) of racemic epoxides [8], both of which have been successfully devised by synthetic chemists. The most prominent catalytic reaction is the Sharpless epoxidation which allows the asymmetric epoxidation of prochiral allylic alcohols [9,10].…”

Section: Introductionmentioning

confidence: 99%

“…Other state of the art protocols, such as the Katsuki-Jacobsen epoxidation of unfunctionalized cis-substituted alkenes [11][12][13], and the Shi's epoxidation of trans-substituted alkenes [14], provide valuable complements to the Sharpless epoxidation. The Jacobsen HKR is one of the most powerful approaches for kinetic resolution of epoxides [8,15]. Even though the maximum theoretical yield of HKR is restricted to 50%, excellent enantiomeric excesses (ee) have been obtained with a diverse of terminal oxides.…”

Section: Introductionmentioning

confidence: 99%

“…Several reviews on the preparation of chiral epoxides have been published [3,7,8,[22][23][24][25][26]. This review does not seek to provide a comprehensive list of all kinds of synthetic/enzymatic methods, but rather to emphasize the potential of biocatalysis in the preparation of chiral epoxides.…”

Section: Introductionmentioning

confidence: 99%

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Biocatalysis as an alternative for the production of chiral epoxides: A comparative review

Lin

Liu

Wang

et al. 2011

Journal of Molecular Catalysis B: Enzymatic

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Section: Classic Methods For the Asymmetric Epoxidation Of Terminal Amentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Biocatalysis as an alternative for the production of chiral epoxides: A comparative review

Lin

Liu

Wang

et al. 2011

Journal of Molecular Catalysis B: Enzymatic

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“…A vast array of examples of enzymatic kinetic resolution are available in the literature and these have been reviewed in detail. [251][252][253] Figure 12 describes examples of enzymatic kinetic resolution of an achiral substrate by acylation, deacylation, oxidation, and reduction. Figure 12 …”

Section: Figure 11mentioning

confidence: 99%

Recent trends in whole cell and isolated enzymes in enantioselective synthesis

Milner¹,

Maguire²

2012

Arkivoc

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Modern synthetic organic chemistry has experienced an enormous growth in biocatalytic methodologies; enzymatic transformations and whole cell bioconversions have become generally accepted synthetic tools for asymmetric synthesis. This review details an overview of the latest achievements in biocatalytic methodologies for the synthesis of enantiopure compounds with a particular focus on chemoenzymatic synthesis in non-aqueous media, immobilisation technology and dynamic kinetic resolution. Furthermore, recent advances in ketoreductase technology and their applications are also presented.Keywords: Biocatalysis, kinetic and dynamic kinetic resolution, Baker's yeast, ketoreductases General IntroductionAsymmetric synthesis is the preferential formation of one stereoisomer of a chiral target compound to another; when scientists at GlaxoSmithKline, AstraZeneca and Pfizer 1 examined 128 syntheses from their companies, they found as many as half of the drug compounds made by their process research and development groups are not only chiral but also contain an average of two chiral centres each. 2In 2006 just 25 % were derived from the chiral pool and over 50 % employed chiral technologies. 1In order to meet regulatory requirements enantiomeric purities of 99.5 % were deemed necessary by the FDA. 3 This is one of the biggest challenges which face chemists today, primarily due to the recognition of the fact that different enantiomers of the same compound can interact differently in biological systems. As a consequence, the production of single enantiomers instead of racemic mixtures has become an important process in the pharmaceutical and agrochemical industry. Several routes can lead to the desired enantiomer including transition metal-, [4][5][6] organo-5,7-10 and bio-catalysis [11][12][13][14][15] and these have been thoroughly reviewed in the literature. 16,17 2. Biocatalysis IntroductionBiocatalysis involves the use of enzymes or whole cells (containing the desired enzyme or enzyme system) as catalysts for chemical reactions. A timeline of historic events in biocatalysis and biotechnology is outlined in Table 1. [18][19][20] Reviews and Accounts Novel methodologies for discovering industrial enzymes based on genomic sequencing and phage display (discussed further in Section 1.3), 21,22 as well as highly effective optimisation tools based on chemical, physical and molecular biology approaches, 23 have improved the access to biocatalysts, increased their stability, and radically broadened their specificity. 24This greater availability of catalysts with superior qualities including the use of new bioengineering tools contributed significantly to the development of new industrial processes. Biocatalytic methodologies for organic synthesis were outlined by Woodley et al. in three categories: established, emerging and expanding chemistries as depicted in Figure 1. 25 Enzyme classesBy the late 1950s it had become evident that the nomenclature of enzymes without any guiding authority, in a period when the...

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