Synthesis and regiochemistry of spiro indane-1,3-dione compounds

Chen, Gang; Zhang, Jie; Wu, Yangjie

doi:10.1007/s11164-011-0357-0

Cited by 10 publications

(4 citation statements)

References 14 publications

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“…2). Nihydrin has been used as carbonyl component in the synthesis of spiropyrrolizidines 15 and 16 in the presence of chalcones and nitrostyrenes, respectively in methanol at rt [20] (Fig. 2).…”

Section: Multicomponent Synthesis Of Pyrrolizidines By Decarboxylativmentioning

confidence: 99%

Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

Nájera

Sansano

2018

Pure and Applied Chemistry

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Different multicomponent 1,3-dipolar cycloadditions (1,3-DC) of cyclic α-amino acid derivatives with aldehydes and dipolarophiles have been described as efficient and simple methodologies for the synthesis of the pyrrolidine unit of pyrrolizidines and indolizidines. When free cyclic α-amino acids are used, a thermal promoted decarboxylative process generates in situ the corresponding non-stabilized azomethine ylides, which afforded the corresponding pyrrolizidines and indolizidines with a hydrogen in the bicyclic units. This methodology has been employed to the synthesis of complex systems including spiro derivatives when ketones are used as carbonyl component. In addition, working with cyclic α-amino acid derived esters, the three-component 1,3-DC takes place under milder reaction conditions giving the corresponding pyrrolizidines and indolizidines with an alkoxycarbonyl group in the bridge adjacent carbon to the nitrogen. This methodology can be carried out by a double consecutive or stepwise 1,3-DC to provide pyrrolizidines via the precursor prolinates. The conformation of the azomethine ylide controls the endo/exo diastereoselectivity of the 1,3-DC.

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Section: Multicomponent Synthesis Of Pyrrolizidines By Decarboxylativmentioning

confidence: 99%

Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

Nájera

Sansano

2018

Pure and Applied Chemistry

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“…This method was later used by Chen and co-workers to prepare similar products. [199][200][201] While the authors claimed that all the reactions proceeded with high regio-and stereoselectivity, it appears that at least the enantiomers of the products (106 and 107) should have formed during the reaction.…”

Section: Pyrrolidines and Pyrrolizidinesmentioning

confidence: 99%

Ninhydrin in synthesis of heterocyclic compounds

Ziarani¹,

Lashgari²,

Azimian³

et al. 2015

Arkivoc

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Ninhydrin has been utilized in many heterocyclic preparations and considered as an important building block in organic synthesis. There is a wide range of reactions that include ninhydrin in the synthesis of heterocyclic compounds. This review highlights the advances in the use of ninhydrin as starting material in the synthesis of various organic compounds and drugs in a fully comprehensive way, from its first isolation in 1910 to the end of 2013. There is also a diversity of multi-component reactions of ninhydrin and we highlight the recent reports in this review.

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“…Attractive π-stacking interactions between π-systems (both aromatic ring and other conjugated systems, even double and triple bonds) play various important roles in diverse phenomena, including the stabilization of biological macromolecules, such as the helical structures of DNA and tertiary structures of proteins, even the complexation of biomolecules and small organic compounds [1][2][3]; the stabilization of the complexation in host-guest systems [4,5]; and controlling selectivities in organic reactions [6][7][8][9]. They can not only control chemoselectivity [10][11][12][13][14] and regioselectivity [15][16][17][18][19] but also stereoselectivities, including diastereoselectivity and enantioselectivity, in diverse organic reactions [20,21]. In 1995, Jones and Chapman wrote a comprehensive review on the π-stacking effect in asymmetric synthesis [20].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in π-Stacking Interaction-Controlled Asymmetric Synthesis

2024

Molecules

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The π-stacking interaction is one of the most important intramolecular and intermolecular noncovalent interactions in organic chemistry. It plays an important role in stabilizing some structures and transition states in certain reactions via both intramolecular and intermolecular interactions, facilitating different selectivities, such as chemo-, regio-, and stereoselectivities. This minireview focuses on the recent examples of the π-stacking interaction-controlled asymmetric synthesis, including auxiliary-induced asymmetric synthesis, kinetic resolution, asymmetric synthesis of helicenes and heterohelicenes, and multilayer 3D chiral molecules.

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Synthesis and regiochemistry of spiro indane-1,3-dione compounds

Cited by 10 publications

References 14 publications

Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

Ninhydrin in synthesis of heterocyclic compounds

Recent Advances in π-Stacking Interaction-Controlled Asymmetric Synthesis

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