Biscinchona alkaloid catalysed Henry reaction of isatins: Enantioselective synthesis of 3-hydroxy-3-(nitromethyl)indolin-2-ones

Parvathaneni, Sai Prathima; Srinivas, K.; Balaswamy, K.; Arundhathi, R.; Reddy, Gajjaia Narsimha; Sridhar, Balasubramanian; Rao, M. Mohan; Likhar, Pravin R.

doi:10.1016/j.tetasy.2011.11.008

Cited by 22 publications

(10 citation statements)

References 66 publications

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“…That same year, another group reported the study of the Henry reaction using the same type of reactants, however they applied a different catalyst (the biscinchona alkaloid C16 -Scheme 12 b)). The use of a bis-cinchona alkaloid as the organocatalyst allowed not only a reduction of the catalyst loading (to 4 mol%, which can be considered a low catalyst load in the field of organocatalysis where 20 mol% loading is generally the norm)), but also a remarkable reduction of the reaction time (from 4 to 5 days to < 14 h) [76]. Another quinidine-based organocatalyst (C17 e Scheme 12 c)) was also reported for the nitroaldol reaction with isatin derivatives [77].…”

Section: Cinchona Alkaloidsmentioning

confidence: 99%

Recent advances in the asymmetric catalytic synthesis of chiral 3-hydroxy and 3-aminooxindoles and derivatives: Medicinally relevant compounds

Brandão

Burke

2018

Tetrahedron

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Several oxindole derivatives, of natural or synthetic origin, have been identified as medicinally appealing compounds, with a plethora of bioactivities reported. Chiral 3-hydroxy and 3-aminooxindole scaffolds have captured the attention of several research groups, due to their importance in drug discovery. In this review, we systematically address the wide variety of asymmetric catalytic methodologies employed in the preparation of these relevant chiral scaffolds, present in many biologically active compounds and/or natural products. Special focus will be given to the nature of the catalyst used.

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Section: Cinchona Alkaloidsmentioning

confidence: 99%

Recent advances in the asymmetric catalytic synthesis of chiral 3-hydroxy and 3-aminooxindoles and derivatives: Medicinally relevant compounds

Brandão

Burke

2018

Tetrahedron

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“…Rao, Likhar et al. reported Henry reactions of nitromethane 124 and isatins and achieved very good results by deployment of the biscinchona catalyst (DHQD) 2 PHAL 132. Furthermore a procedure using recoverable guanidinium salts for the catalysis of Henry reactions was developed 133…”

Section: Henry Reaction and Related Reactionsmentioning

confidence: 99%

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

Scheffler

Mahrwald

2013

Chemistry A European J

191

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Beyond a doubt organocatalysis belongs to the most exciting and innovative chapters of organic chemistry today. Organocatalysis has emerged not only as a complement to metal-catalyzed reactions and to biocatalysis over the last decade, but also provides new asymmetric organocatalyzed reactions that cannot be accomplished by metal- or biocatalyzed reactions so far. A large number of organocatalytic processes are already well established in organic synthesis. Nevertheless, the number of publications in this field is still on the increase; new important results are produced constantly. This review gives a detailed overview of the latest developments and main streams in organocatalyzed asymmetric CC bond formation processes of the last three years. It is intended to outline the most important current findings focused on especially new synthetic methodologies.

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“…Final Henry adducts 57 were obtained with high yields (up to 98%) and high enantioselectivities (up to 97% ee) ( Figure 13). [65]…”

Section: Enantioselective Henry Reactionmentioning

confidence: 99%

Isatin as a Strategic Motif for Asymmetric Catalysis

et al. 2013

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Biscinchona alkaloid catalysed Henry reaction of isatins: Enantioselective synthesis of 3-hydroxy-3-(nitromethyl)indolin-2-ones

Cited by 22 publications

References 66 publications

Recent advances in the asymmetric catalytic synthesis of chiral 3-hydroxy and 3-aminooxindoles and derivatives: Medicinally relevant compounds

Recent advances in the asymmetric catalytic synthesis of chiral 3-hydroxy and 3-aminooxindoles and derivatives: Medicinally relevant compounds

Recent Advances in Organocatalytic Methods for Asymmetric CC Bond Formation

Isatin as a Strategic Motif for Asymmetric Catalysis

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