Organocatalytic asymmetric approach to spirocyclic tetrahydrothiophenes containing either a butenolide or an azlactone structural motif

Hejmanowska, Joanna; Albrecht, Łukasz

doi:10.3998/ark.5550190.p009.622

Cited by 5 publications

(2 citation statements)

References 48 publications

(59 reference statements)

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“…Additionally, a chiral Brønsted base, derived from cinchona alkaloids was used to achieve enantioselectivity. (Scheme ) . The stereochemistry of the synthesized compounds was confirmed by 2D NOE analysis.…”

Section: Spiro δβγ‐Butenolidesmentioning

confidence: 95%

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Yadav

Pratap

Ram³

2020

Asian J Org Chem

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Spirobutenolides and spirobutyrolactones structural motifs are widespread in various natural products that exhibit a broad array of biological activities. Additionally, their synthetic analogues also serve as biologically active compounds and building blocks of complex molecules. Owing to the wide range of pharmacological activities and structural diversity of the spirobutenolides and spirobutyrolactones, various efficient synthetic methodologies have been established to construct such interesting scaffolds. In the past decades, numerous total syntheses of spirobutenolides and spirobutyrolactones containing natural products have been reported. Structurally diverse spirobutenolides and spirobutyrolactones have been synthesized by using singlet oxygen, Mannich reaction, aldol condensation, rearrangement reaction , Reformatsky reaction, Michael-addition cyclization, Diels-Alder reaction, photocyclization reaction, and pericyclic reactions. Recently, metal-catalyzed cyclization, photocatalyzed radical cyclization, Baylis-Hillman reaction, asymmetric organocatalysis, NHC catalysis, ring contraction reactions, and hypervalent iodine catalysis have emerged as powerful tools to architect these nuclei. This review gives an overview of advancements in chemically and biologically relevant spirobutenolides and spirobutyrolactones of natural and synthetic origin. It also covers the newer methodologies for the construction of natural as well as synthetic spirobutenolides and spirobutyrolactones along with their potential applications.

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Section: Spiro δβγ‐Butenolidesmentioning

confidence: 95%

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Yadav

Pratap

Ram³

2020

Asian J Org Chem

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“…Due to the 2(3 H )‐furanones (butenolide) motif present in various biologically relevant molecules, it has been applied in a broad target‐oriented organic synthesis. An efficient methodology to synthesize spiro butanolide bearing tetrahydrothiophenes was reported by Albrecht's group [16] in 2016. They applied 1,4‐dithiane‐2,5‐diol 1 and unsaturated γ ‐lactones 10 to this cascade process, with the 20 mol% of C5 as the catalyst, followed by acetylation using acetic anhydride, the acetylated spirocyclic product 11 could be obtained smoothly (Scheme 5a).…”

Section: Asymmetric Sulfa‐michael/aldol (Henry) Cascade Reactionsmentioning

confidence: 99%

Recent Advances in Organocatalyzed Asymmetric Sulfa‐Michael Addition Triggered Cascade Reactions

Niu

2023

The Chemical Record

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The sulfa‐Michael addition reaction is a crucial subset of the Michael addition reaction, and aroused the interest of numerous synthetic biologists and chemists. In particular, sulfa‐Michael addition triggered cascade reaction has developed quickly in recent years because it offers an efficient method to construct C−S bonds and other bonds in one approach, which is widely applicable for building chiral pharmaceuticals, their intermediates, and natural compounds. This review emphasizes the recent advancements in sulfa‐Michael addition‐triggered cascade reactions for the stereoselective synthesis of sulfur‐containing compounds, including sulfa‐Michael/aldol, sulfa‐Michael/Henry, sulfa‐Michael/Michael, sulfa‐Michael/Mannich and some sulfa‐Michael triggered multi‐step processes. Moreover, some reaction mechanisms and derivatization experiments are introduced appropriately.

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1,4‐Dithiane‐2,5‐diol: An Attractive Platform for the Synthesis of Sulfur‐Containing Functionalized Heterocycles

2018

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This microreview highlights the utility of 1,4‐dithiane‐2,5‐diol (1) as a source for the in situ generation of 2‐mercaptoacetaldehyde (2), a versatile two‐carbon synthon featuring both electrophilic and nucleophilic reaction centres and widely utilized as an attractive platform for the preparation of sulfur‐containing molecules. We discuss the chemistry involved, mainly focusing on its applications to the construction of sulfur‐containing heterocyclic compounds including the thiophene and 1,3‐thiazole families and other different sulfur–nitrogen and sulfur–oxygen heterocycles that continue to be a pillar of organic synthesis as a result of their broad application in organic and medicinal chemistry.

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Organocatalytic asymmetric approach to spirocyclic tetrahydrothiophenes containing either a butenolide or an azlactone structural motif

Cited by 5 publications

References 48 publications

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Natural and Synthetic Spirobutenolides and Spirobutyrolactones

Recent Advances in Organocatalyzed Asymmetric Sulfa‐Michael Addition Triggered Cascade Reactions

1,4‐Dithiane‐2,5‐diol: An Attractive Platform for the Synthesis of Sulfur‐Containing Functionalized Heterocycles

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