Enzymatic enantioselective aldol reactions of isatin derivatives with cyclic ketones under solvent-free conditions

Liu, Zhiqiang; Xiang, Zhongzheng; Shen, Zhou; Wu, Qi; Lin, Xianfu

doi:10.1016/j.biochi.2014.01.006

Cited by 33 publications

(19 citation statements)

References 59 publications

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“…Various amino acid salts catalysts screened for aldol reaction. [11][12][13][14]. On the contrary, they may hinder the enantioselective synthesis of the product.…”

Section: Resultsmentioning

confidence: 99%

Natural amino acid salt catalyzed aldol reactions of isatins with ketones: highly enantioselective construction of 3-alkyl-3-hydroxyindolin-2-ones

Gong

et al. 2015

Tetrahedron: Asymmetry

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“…Various amino acid salts catalysts screened for aldol reaction. [11][12][13][14]. On the contrary, they may hinder the enantioselective synthesis of the product.…”

Section: Resultsmentioning

confidence: 99%

Natural amino acid salt catalyzed aldol reactions of isatins with ketones: highly enantioselective construction of 3-alkyl-3-hydroxyindolin-2-ones

Gong

et al. 2015

Tetrahedron: Asymmetry

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“…In separate work in 2014, nuclease p1 ( 6 ) was used for solvent‐free asymmetric aldol reaction of isatin derivatives and cyclic ketones . In the presence of deionized water as an additive, catalyst 6 could deliver the desired products in high yields (up to 95 %) and moderate to good stereoselectivities (dr up to >99/1, ee up to 82 %) (Scheme ).…”

Section: Solvent‐free Reactions In Asymmetric Catalysismentioning

confidence: 99%

Recent Advances in Solvent‐Free Asymmetric Catalysis

2019

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It is well‐known that solvent is one of the most important factors that affect chemical reactions. This factor is more noticeable and impressive in the asymmetric reactions where the effective interaction of reactants and the creation of a uniform chiral environment is necessary. Nevertheless, when reactions are carried out in the absence of solvent, some privileged advantages such as easy work up, short reaction time, lack of waste solvents, and following the green chemistry principles, are appeared. Therefore, according to the importance of asymmetric synthesis and green chemistry, solvent‐free asymmetric catalysis can act as a considerable and necessary subject in synthetic chemistry. In this review, we have a survey on the solvent‐free asymmetric synthesis by the use of either homogeneous or heterogeneous chiral catalysts.

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“…While earlier, there was a strong focus on the use of lipases for C-C bond formation reactions [38,40,41,48,49], use of other enzymes in catalyzing diverse kinds of reactions is being increasingly demonstrated. Liu et al [50] have reported asymmetric aldol reactions between isatin derivatives with cyclic ketones catalyzed by nuclease p1 from Penicillium citrinum. This example of catalytic promiscuity provides a green approach for the synthesis of pharmaceutically active compounds.…”

Section: Catalytic Promiscuity: Beyond Lipasesmentioning

confidence: 99%

Enzyme promiscuity: using the dark side of enzyme specificity in white biotechnology

Arora

Mukherjee

Gupta

2014

Sustain Chem Process

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Enzyme promiscuity can be classified into substrate promiscuity, condition promiscuity and catalytic promiscuity. Enzyme promiscuity results in far larger ranges of organic compounds which can be obtained by biocatalysis. While early examples mostly involved use of lipases, more recent literature shows that catalytic promiscuity occurs more widely and many other classes of enzymes can be used to obtain diverse kinds of molecules. This is of immense relevance in the context of white biotechnology as enzyme catalysed reactions use greener conditions.

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Enzymatic enantioselective aldol reactions of isatin derivatives with cyclic ketones under solvent-free conditions

Cited by 33 publications

References 59 publications

Natural amino acid salt catalyzed aldol reactions of isatins with ketones: highly enantioselective construction of 3-alkyl-3-hydroxyindolin-2-ones

Natural amino acid salt catalyzed aldol reactions of isatins with ketones: highly enantioselective construction of 3-alkyl-3-hydroxyindolin-2-ones

Recent Advances in Solvent‐Free Asymmetric Catalysis

Enzyme promiscuity: using the dark side of enzyme specificity in white biotechnology

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