Water—More Than Just a Green Solvent: A Stereoselective One‐Pot Access to All‐Chiral Tetrahydronaphthalenes in Aqueous Media

Tan, Bin; Zhu, Di; Zhang, Lihong; Chua, Pei Juan; Zeng, Xiaofei; Zhong, Guofu

doi:10.1002/chem.200902932

Cited by 48 publications

(11 citation statements)

References 84 publications

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“…Tan et al. described tandem Michael addition/intramolecular [3+2] cycloaddition in water (Scheme ) . Jørgensen–Hayashi catalyst ( C6 ) enabled the formation of products 170 with high enantiomeric purity (99 % ee ) and dr (99:1).…”

Section: Water As a Medium For Organocatalytic Reactionsmentioning

confidence: 99%

Green Asymmetric Organocatalysis

et al. 2020

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Scheme12. At extile-supported organocatalyst for anhydride opening; MTBE = methyl tert-butyl ether.Scheme13. Organocatalytic aldolreaction conductedb yu sing the continuous-flow technique.Scheme11. PS-immobilized catalyst C32 for the amination of oxindoles 32.Scheme40. Photo-organocatalytic hydroxylation of ketoesters and amides. LED = light-emitting diode.Scheme41. Light-promoted cyclization.Scheme42. Light-promoted alkylation of aldehydes. EWG = electron-withdrawinggroup.Scheme49. Primary-aminec atalyzed light-promoted alkylations of dicarbonyl compounds.Scheme48. Light-promoted organocatalytic Michael additions.

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Section: Water As a Medium For Organocatalytic Reactionsmentioning

confidence: 99%

Green Asymmetric Organocatalysis

et al. 2020

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“…In 2010, Zhong and co‐workers disclosed an efficient stereoselective synthesis of tetrahydronaphthalene‐fused isoxazolidine derivatives 15 involving the reaction between nitroolefin acrylates 12 , aldehydes 13 and aryl‐ or benzylhydroxylamines in aqueous medium in the presence of the Hayashi–Jørgensen catalyst 14 . As shown in Scheme , the reaction tolerated a variety of enolizable aldehydes and hydroxylamines to afford the products in good yields with excellent enantioselectivities (up to >99% ee ) …”

Section: Synthesis Of Five‐membered Heterocyclesmentioning

confidence: 99%

Proline and its Derivatives as Organocatalysts for Multi‐ Component Reactions in Aqueous Media: Synergic Pathways to the Green Synthesis of Heterocycles

et al. 2019

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Proline is a non‐toxic and inexpensive natural amino acid that is readily available in both enantiomeric forms and was one of the very first compounds to be studied as an organocatalyst. Proline can engage in several modes of organocatalysis, as it can behave both as a Brønsted acid or a Brønsted base, and it can also easily generate the iminium or enamine intermediates that are typical of covalent organocatalysis. In view of the importance of diminishing the generation of residues formed by volatile organic solvents, the development of synthetically useful reactions that can be performed in aqueous environments is of increasing significance. The synergic combination of the advantages of water as a reaction medium with the efficiency associated to reactions that are able to generate several bonds in one operation is particularly relevant from the point of view of sustainable chemistry. In this review we critically summarize the use of proline and proline derivatives as catalysts of multi‐component reactions performed in aqueous media and leading to synthetically and biologically relevant heterocycles, a very important class of compounds that constitutes over 60% of drugs and agrochemicals.

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“…When used with nitrostyrene acrylates an access to the corresponding tetrahydronaphthalenes is given 255. For cinchona alkaloid catalyzed Michael‐cycloadditions of nitrostyrenes with allylmalonates see reference 256.…”

Section: Multicomponent and Cascade Reactionsmentioning

confidence: 99%

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

Scheffler

Mahrwald

2013

Chemistry A European J

197

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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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Water—More Than Just a Green Solvent: A Stereoselective One‐Pot Access to All‐Chiral Tetrahydronaphthalenes in Aqueous Media

Cited by 48 publications

References 84 publications

Green Asymmetric Organocatalysis

Green Asymmetric Organocatalysis

Proline and its Derivatives as Organocatalysts for Multi‐ Component Reactions in Aqueous Media: Synergic Pathways to the Green Synthesis of Heterocycles

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

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