Enantioselective assembly of functionalized carbocyclic spirooxindoles using an<scp>l</scp>-proline derived thiourea organocatalyst

Gajulapalli, V. Pratap Reddy; Vinayagam, Poopathy; Kesavan, Venkitasamy

doi:10.1039/c4ra13711f

Cited by 40 publications

(17 citation statements)

References 55 publications

(9 reference statements)

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“…To avoid the heated conditions, in 2015, Kesavan et al. used l ‐proline derived bifunctional thiourea catalyst to address this reaction, and a broader substrate scope with excellent stereoselectivity was disclosed …”

Section: Direct Strategiesmentioning

confidence: 99%

Organocatalytic Asymmetric Vinylogous Michael Reactions

Yin

Jiang

2017

ChemCatChem

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Since R. C. Fuson formulated the principle of vinylogy, this platform has been extensively developed through combining diverse predominant chemical transformations. Among them, asymmetric vinylogous Michael reaction has been recognized as an efficient method to build chiral 1,7‐dioxo C chains (1,9‐dioxo C chains for bisvinylogous manifold) with diverse functional groups, which provides robust approaches to access numerous chiral compounds with pharmaceutical importance. In this review, the advances in the area of organocatalytic asymmetric vinylogous Michael reactions on the period from 2014 to nowadays are discussed, including the current scope, limitations of the transformations and applications in asymmetric synthesis of complex and valuable compounds.

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Section: Direct Strategiesmentioning

confidence: 99%

Organocatalytic Asymmetric Vinylogous Michael Reactions

Yin

Jiang

2017

ChemCatChem

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“…Electrophilic isatilydene malonitrile derivatives 9 are substrates of choice to promote Michael addition/cyclization transformations through reaction with nucleophiles. In 2015, Kesavan and co-workers have indeed devised a sequential vinylogous Michael addition/cyclization in the presence of vinyl malononitriles 19 and 20 as vinylogous nucleophiles [ 28 ]. The reaction, conducted in the presence of L -proline derived bifunctional thiourea catalyst XI (10 mol %) in toluene at 0 °C, demonstrated a wide scope with both substrates ( Scheme 6 , compounds 21 and 22 ).…”

Section: Thiourea-based 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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“…As part of our ongoing interest in the development of new and efficient synthetic strategies for the synthesis of biologically important oxindole‐fused spiro heterocyclic systems and spiro carbocyclic systems, we planned to synthesize the spirocarbocyclic oxindole framework through the Hauser annulation of phthalides. There is no precedent in the literature for the use of oxindole‐based Hauser acceptors.…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of Highly Functionalized Spirocarbocyclic Oxindoles through Hauser Annulation

Lokesh

Kesavan

2017

Eur J Org Chem

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Enantioselective assembly of functionalized carbocyclic spirooxindoles using anl-proline derived thiourea organocatalyst

Abstract: Enantioselective sequential vinylogous Michael addition–cyclization reactions of vinyl malononitriles with isatylidene malononitrile were accomplished usingl-proline derived bifunctional thiourea.

Cited by 40 publications

References 55 publications

Organocatalytic Asymmetric Vinylogous Michael Reactions

Organocatalytic Asymmetric Vinylogous Michael Reactions

Non-Covalent Organocatalyzed Domino Reactions Involving Oxindoles: Recent Advances

Efficient Synthesis of Highly Functionalized Spirocarbocyclic Oxindoles through Hauser Annulation

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