Diastereoselective construction of a library of structural bispiro[butyrolactone/valerolactone–pyrrolidine–indanedione] hybrids <i>via</i> 1,3-dipolar cycloaddition reactions

Zhang, Lei; Wei, Qufu; Liu, Ren-Ming; Tian, You‐Ping; Pan, Bowen; Liu, Xiong‐Li

doi:10.1039/d2nj01571d

Cited by 4 publications

(4 citation statements)

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition, using α-isothiocyanato lactone and methyleneindolinone as the reactants, another organocatalytic synthesis of an optically active bispiro[oxindole-butyrolactone] scaffold was also reported by Cao et al [53] The product having three contiguous stereocenters, including two spiro-quaternary chiral centers, was isolated with > 99% ee, > 20:1 dr and in 80% yield.…”

Section: -Isothiocyanato Butyrolactones As C-n-c Synthonsmentioning

confidence: 87%

Section: Benzolactone-derived Olefins As 2c Synthonsmentioning

confidence: 98%

“…In this context, an efficient organocatalyzed asymmetric sequential Michael/cyclization of α-isothiocyanato imide 24 with benzothiolactone 1 under mild conditions was reported by Cao et al [53] . However, only two sulfur-containing 3,3'-pyrrolidonyl spirobenzolactones 25 and 26 were reported [53] . Notably, when the oxygen atom of benzolactone-derived olefin 1 was replaced by sulfur, the enantioselective Michael/Cyclization reaction of thiobenzolactone-derived olefin 1 with α-isothiocyanato imide 24 also proceeded smoothly, which provided the spirothiobenzolactone skeleton 26 with greater than 99% ee and moderate distereoselectivity [Scheme 11].…”

Section: Benzolactone-derived Olefins As 2c Synthonsmentioning

confidence: 98%

“…Organocascade Michael/Cyclization reaction of benzolactone-derived olefin 1 with α-isothiocyanato imide 24. This figure is used with permission from John Wiley and Sons Ltd [53] .…”

Section: α β-Unsaturated Butyrolactones/valerolactones As 2c Synthonsmentioning

confidence: 99%

See 3 more Smart Citations

Recent advances in organocatalytic cascade reactions for enantioselective synthesis of chiral spirolactone skeletons

Yang¹,

Pan²,

Chen³

et al. 2023

Chem Synth

View full text Add to dashboard Cite

Chiral spirolactones, including spiropropyllactones, spirobutyrolactones, and spirovalerolactones, are important heterocyclic frameworks that attracted the attention of organic and medicinal chemists because these motifs constitute the core structure of several natural products and bioactive molecules. The absolute configuration and the substituents on the fully substituted spirocyclic stereocenter of the lactone can potentially enhance specificity for ligand-protein binding and enhance bioavailability, potency, and metabolic stability. So, intensive attention from chemists has been paid to the synthetic methods leading to such prominent structural motifs. The synthetic methods can be divided into two main classes. The first approach takes advantage of the presence of the existing lactone structure and focuses on its functionalization. The second approach is the lactone framework constructed from various precursors in a direct spirolactonization reaction. In this review, for convenience in reading, the recent advances in the synthesis of spirolactones are summarized and discussed according to the two major organocatalytic asymmetric synthetic routes: (i) using the lactone-related frameworks as building blocks; and (ii) direct spirolactonization reaction using various reagents. This review also describes both the mechanisms and related transformations, and gives some insights into challenging issues in this research field, which will enlighten the future development of this field.

show abstract

Section: -Isothiocyanato Butyrolactones As C-n-c Synthonsmentioning

confidence: 87%

Section: Benzolactone-derived Olefins As 2c Synthonsmentioning

confidence: 98%

Section: Benzolactone-derived Olefins As 2c Synthonsmentioning

confidence: 98%

“…Organocascade Michael/Cyclization reaction of benzolactone-derived olefin 1 with α-isothiocyanato imide 24. This figure is used with permission from John Wiley and Sons Ltd [53] .…”

Section: α β-Unsaturated Butyrolactones/valerolactones As 2c Synthonsmentioning

confidence: 99%

See 2 more Smart Citations

Recent advances in organocatalytic cascade reactions for enantioselective synthesis of chiral spirolactone skeletons

Yang¹,

Pan²,

Chen³

et al. 2023

Chem Synth

View full text Add to dashboard Cite

show abstract

A review on 2-arylidene-1,3-indanediones: preparation and applications to the synthesis of diverse spirocyclic compounds

Chitteti,

Padmaja,

Rani

et al. 2024

Monatsh Chem

View full text Add to dashboard Cite

An Energetic and Topological Approach to Understanding the Interplay of Noncovalent Interactions in a Series of Crystalline Spiropyrrolizine Compounds

Tsering,

Dey,

Kapoor

et al. 2024

ACS Omega

View full text Add to dashboard Cite

Synthesis of quinoline-containing spiropyrrolizine was achieved via a 1,3-dipolar cycloaddition reaction of azomethine ylide (generated in situ from ninhydrin and l-proline) and (E)-2-styrylquinoline. The synthesized compounds were characterized by 1H NMR, 13C NMR, HRMS, and single-crystal XRD analysis. The XRD data revealed that the solid-state structures of the compounds belong to the monoclinic system of the space group P21/c and are stabilized through various weak noncovalent interactions such as C–H···O, C–H···π, and π···π interactions. The noncovalent interactions are characterized and quantified through Hirshfeld surface analysis. Moreover, the interaction energies of the intermolecular noncovalent interactions are calculated through PIXEL calculation. The PIXEL calculation provides precise interaction energy with an energy decomposition scheme. Energy Framework calculations have also been performed to delve deeper into understanding the intermolecular interactions. The intermolecular interactions are further characterized using Bader’s theory of “atoms in molecules” (QTAIM) and the “noncovalent” (NCI) interaction plot index. The nature and strength of noncovalent interactions are analyzed from the topological parameters at (3, −1) bond critical points (BCPs).

show abstract

Diastereoselective construction of a library of structural bispiro[butyrolactone/valerolactone–pyrrolidine–indanedione] hybrids via 1,3-dipolar cycloaddition reactions

Abstract: Herein, a highly efficient strategy that allows the diversity synthesis of a library of structural bispiro[butyrolactone-pyrrolidine-indanedione] hybrids is achieved effectively by means of 1,3-dipolar cycloadditions of α,β-unsaturated butyrolactones/valerolactones as dipolarophiles...

Cited by 4 publications

References 64 publications

Recent advances in organocatalytic cascade reactions for enantioselective synthesis of chiral spirolactone skeletons

Recent advances in organocatalytic cascade reactions for enantioselective synthesis of chiral spirolactone skeletons

A review on 2-arylidene-1,3-indanediones: preparation and applications to the synthesis of diverse spirocyclic compounds

An Energetic and Topological Approach to Understanding the Interplay of Noncovalent Interactions in a Series of Crystalline Spiropyrrolizine Compounds

Contact Info

Product

Resources

About