Organocatalytic Asymmetric Synthesis of Spirooxindole Embedded Oxazolidines

Parida, Chandrakanta; Mondal, Buddhadeb; Ghosh, Animesh; Pan, Subhas Chandra

doi:10.1021/acs.joc.1c00644

Cited by 12 publications

(9 citation statements)

References 67 publications

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“…Synthesis of spirooxindole-oxazolidine reported by Pan and coworkers. [96] Scheme 5. Synthesis of pyrano [2,3-c]pyrazole embedded spiro oxindole reported by Sha, Wu, and co-workers.…”

Section: Michael/alkylation or N-hemiketalization Cascade Reactionsmentioning

confidence: 99%

“…The chiral center of the hemiaminal is assumed to be stable, so the final product ( 4 ) is produced by an aza‐Michael step that exhibits good diastereoselectivity ( dr up to 5.5 : 1) (Scheme 4). [96] Wu et al. successfully used N ‐heterocycles as 1,3‐bisnucleophiles with isatylidene malononitrile derivatives in the presence of a chiral organocatalyst based on a tertiary amine (Cat.4) in ethyl acetate to afford enantioselective pyrano[2,3‐ c ]pyrazole‐embedded spiro‐oxindole derivatives ( 8 ) ( ee up to 91 %).…”

Section: Michael Cascade Cyclization Reactions For Spiro Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…To give readers a clear idea, this review is primarily organized by spiro derivatives through stereoselective Michael cascade cyclization reactions [94–113] . This first section is organized by the type of Michael cascade cyclization reactions, i. e., Michael spiro‐cyclization, [94–98] Michael/ N ‐hemiketalization or alkylation reaction, [99–103] Michael–Michael aldol reaction, [104–107] double Michael addition cyclization reaction, [108–110] and oxa/aza Michael cascade reaction [111–113] . The second part of this review is devoted to stereoselective multicomponent cycloaddition reactions, [114–121] and the third section contains diastereoselective approaches [122–135] and some miscellaneous reactions [136–140] to form spiro‐hetero/carbocycles.…”

Section: Introductionmentioning

confidence: 99%

“…To give readers a clear idea, this review is primarily organized by spiro derivatives through stereoselective Michael cascade cyclization reactions. [94][95][96][97][98][99][100][101][102][103][104][105][106][107][108][109][110][111][112][113] This first section is organized by the type of Michael cascade cyclization reactions, i. e., Michael spiro-cyclization, [94][95][96][97][98] Michael/N-hemiketalization or alkylation reaction, [99][100][101][102][103] Michael-Michael aldol reaction, [104][105][106][107] double Michael addition cyclization reaction, [108][109][110] and oxa/aza Michael cascade reaction. [111][112][113] The second part of this review is devoted to stereoselective multicomponent cycloaddition reactions, [114][115][116][117][118]…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Stereoselective Multicomponent Reactions for the Synthesis of Spiro Derivatives: Recent Progress

Patel

2022

Eur J Org Chem

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Spiro derivatives are important scaffolding substances found in many natural products and pharmaceuticals. In the last decade, numerous new approaches based on multicomponent reactions have been explored for the selective and efficient development of new spiro derivatives using various organocatalytic and transition metal‐based catalytic systems. This Review discusses pioneering advances in the field of catalytic stereoselective multicomponent reactions for the preparation of various spiro derivatives. These include stereoselective Michael cascade cyclization reactions, cycloadditions, diastereoselective reactions, and miscellaneous reactions for the synthesis of spiro‐hetero/carbocycles. Advances in the last decade have made it possible to synthesize various spiro compounds with good to excellent stereoselectivity under appropriate reaction conditions. However, achieving high regioselectivity in several described multicomponent reactions remains a challenge. Organocatalysts and transition‐metal‐based catalysts play a crucial role in achieving this milestone. Proposed catalytic mechanisms and supporting evidence are highlighted in this Review. The progress described in catalytic stereoselective approaches for spiro derivatives is immense. However, it is expected that new stereoselective synthetic methods will soon be developed that can be widely used for the preparation of spiro‐heterocycles/carbocycles.

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“…Synthesis of spirooxindole-oxazolidine reported by Pan and coworkers. [96] Scheme 5. Synthesis of pyrano [2,3-c]pyrazole embedded spiro oxindole reported by Sha, Wu, and co-workers.…”

Section: Michael/alkylation or N-hemiketalization Cascade Reactionsmentioning

confidence: 99%

Section: Michael Cascade Cyclization Reactions For Spiro Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Catalytic Stereoselective Multicomponent Reactions for the Synthesis of Spiro Derivatives: Recent Progress

Patel

2022

Eur J Org Chem

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Base‐catalyzed [3 + 2]/[4 + 2]‐annulations of cyclic N‐sulfimines with γ‐ and δ‐sulfonamido/hydroxy‐α,β‐unsaturated carbonyls: Stereoselective synthesis of imidazolidines, oxazolidines, hexahydropyrimidines, and 1,3‐oxazinanes

Kim

2023

Bulletin Korean Chem Soc

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A highly efficient and straightforward synthetic methodology has been established for the preparation of imidazolidine derivatives through the [3 + 2]‐annulation of cyclic N‐sulfimines. This reaction involves the reaction of cyclic N‐sulfimines and γ‐sulfonamido‐α,β‐unsaturated carbonyl compounds, with Cs2CO3 serving as the catalyst. The outcome is a diverse range of imidazolidine derivatives with remarkable yields and stereoselectivities. In addition, the [4 + 2]‐annulation between cyclic N‐sulfimines and δ‐sulfonamido‐α,β‐unsaturated carbonyl compounds, catalyzed by Et3N, has been successfully applied for the synthesis of stereoselective hexahydropyrimidines. Furthermore, the base‐catalyzed annulation of cyclic N‐sulfimines with γ‐ and δ‐hydroxy‐α,β‐unsaturated carbonyl compounds has proven to be a reliable method for the synthesis of oxazolines and 1,3‐oxazinanes.

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Base‐Promoted [3+3]‐Cycloaddition of γ‐Hydroxy‐α,β‐unsaturated Carbonyls with N,N′‐Cyclic Azomethine Imines for Synthesizing Bicyclic Oxadiazines

2022

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A novel approach of [3+3]‐cycloaddition of N,N′‐cyclic azomethine imines with γ‐hydroxy‐α,β‐unsaturated carbonyls was developed. Bicyclic oxadiazines were readily obtained in moderate to good yields from the reactions of various γ‐hydroxy‐α,β‐unsaturated ketones, including aromatic and aliphatic ketones, with N,N′‐cyclic azomethine imines under mild conditions, demonstrating the broad substrate scope.

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Organocatalytic Asymmetric Synthesis of Spirooxindole Embedded Oxazolidines

Cited by 12 publications

References 67 publications

Catalytic Stereoselective Multicomponent Reactions for the Synthesis of Spiro Derivatives: Recent Progress

Catalytic Stereoselective Multicomponent Reactions for the Synthesis of Spiro Derivatives: Recent Progress

Base‐catalyzed [3 + 2]/[4 + 2]‐annulations of cyclic N‐sulfimines with γ‐ and δ‐sulfonamido/hydroxy‐α,β‐unsaturated carbonyls: Stereoselective synthesis of imidazolidines, oxazolidines, hexahydropyrimidines, and 1,3‐oxazinanes

Base‐Promoted [3+3]‐Cycloaddition of γ‐Hydroxy‐α,β‐unsaturated Carbonyls with N,N′‐Cyclic Azomethine Imines for Synthesizing Bicyclic Oxadiazines

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