Organocatalytic Asymmetric Michael/Cyclization Cascade Reaction of 3‐Isothiocyanato Oxindoles with Maleimides for the Efficient Construction of Pyrrolidonyl Spirooxindoles

Liu, Lei; Zhao, Bo‐Liang; Du, Da‐Ming

doi:10.1002/ejoc.201600658

Cited by 29 publications

(9 citation statements)

References 35 publications

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“…Du and co‐workers also reported an asymmetric domino Michael/cyclization reaction between 3‐isothiocyanatooxindoles 409 and maleimide derivatives 609 for the synthesis of pyrrolidonyl spirooxindoles 610 (Scheme ) …”

Section: Multifunctional Catalystsmentioning

confidence: 99%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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Sustainability in chemical synthesis is a major aspect of the current synthetic endeavors and, therefore,m imicking the biological process in the laboratory nowadays has the highest priority.T owards achieving this goal, designingorganic reactions in domino mode rathert han the multistep synthetic pathways andu sing organocatalysisi nstead of metal catalysis have received al ot of attention due to the inherenta dvantageso ft hese processes in terms of synthetic efficiencya nd sustainability.A saresult, the field of asymmetric organocatalytic domino reactions has witnessed tremendous progress in recent years.T his review attempts to summarize the latest developments in asymmetric organocatalyzed domino reactions since 2012, with the emphasis on the catalysts andr eactionm odes.D iscussions on the reactionm echanismsa nd the applications of the developed domino reactionm ethodsi nt he synthesis of biologically active molecules and natural products are also includedwhen appropriate.

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Section: Multifunctional Catalystsmentioning

confidence: 99%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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“…and >99% ee). 79 Zhao and Du et al applied the same strategy, using as the alkene unsaturated barbiturates 80 and maleimides 81 The reaction comprises a Michael-Michael-aldol sequence in the presence of two different catalysts (secondary amine catalysts L or LI and a bifunctional thiourea/tertiary amine catalyst XLIX). The reaction tolerates aromatic and aliphatic enals as well as aromatic and aliphatic nitroalkenes; however, a decrease in diastereoselectivity and yield was observed when aliphatic starting materials were employed.…”

Section: Scheme 46: Spirocyclization Reported By Shi and Xumentioning

confidence: 99%

New development in the enantioselective synthesis of spiro compounds

et al. 2018

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The enantioselective synthesis of spirocycles has long been pursued by organic chemists. Despite their unique 3D properties and presence in several natural products, the difficulty in their enantioselective synthesis makes them underrepresented in pharmaceutical libraries. Since the first pioneering reports of the enantioselective construction of spirosilanes by Tamao et al., significant effort has been devoted towards the development of new promising asymmetric methodologies. Remarkably, with the advent of organocatalysis, particularly over six years, the reported methodologies for the synthesis of spirocycles have increased exponentially. The aim of this review is to summarize the latest trends and developments in the enantioselective synthesis of spirocompounds during these last six years.

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“…Exploiting the well-known reactivity of 3-isothiocyano oxindoles conferred by the strongly electron withdrawing NCS group, Du and co-workers reported also the preparation of more complex pyrrolidinyl spirooxindoles employing either chalcones 82 [ 57 ] or maleimides 84 [ 58 ] as acceptor counterpart ( Scheme 25 ). In both cases the extremely similar quinine-derived squaramide XXVII (10 mol %) and XXVIII (5 mol %) resulted to be the best catalysts in the same reaction condition (i.e., CH 2 Cl 2 , 0 °C).…”

Section: Squaramide Catalystsmentioning

confidence: 99%

Non-Covalent Organocatalyzed Domino Reactions Involving Oxindoles: Recent Advances

et al. 2017

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The ubiquitous presence of spirooxindole architectures with several functionalities and stereogenic centers in bioactive molecules has been appealing for the development of novel methodologies seeking their preparation in high yields and selectivities. Expansion and refinement in the field of asymmetric organocatalysis have made possible the development of straightforward strategies that address these two requisites. In this review, we illustrate the current state-of-the-art in the field of spirooxindole synthesis through the use of non-covalent organocatalysis. We aim to provide a concise overview of very recent methods that allow to the isolation of unique, densely and diversified spirocyclic oxindole derivatives with high structural diversity via the use of cascade, tandem and domino processes.

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Organocatalytic Asymmetric Michael/Cyclization Cascade Reaction of 3‐Isothiocyanato Oxindoles with Maleimides for the Efficient Construction of Pyrrolidonyl Spirooxindoles

Cited by 29 publications

References 35 publications

Recent Progress in Organocatalytic Asymmetric Domino Transformations

Recent Progress in Organocatalytic Asymmetric Domino Transformations

New development in the enantioselective synthesis of spiro compounds

Non-Covalent Organocatalyzed Domino Reactions Involving Oxindoles: Recent Advances

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