Organocatalytic enantioselective synthesis of dihydronaphthofurans and dihydrobenzofurans: reaction development and insights into stereoselectivity

Susam, Zeynep Dilşad; ÖZcan, B.; Kurtkaya, Enis; Yıldırım, Erol; Tanyeli, Cihangir

doi:10.1039/d2ob01571d

Cited by 3 publications

(1 citation statement)

References 43 publications

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“…[16] The catalysts devel-oped in our research group gave outstanding results in a wide variety of asymmetric transformation-type reactions. [14,17]…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of Trifluoromethyl Substituted Spiro[Indoline‐3,4′‐Pyrano[2,3‐c]Pyrazole] Derivatives with Organocatalysts

Özcan,

Kömüşdoğan,

Şahin

et al. 2024

ChemistrySelect

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Spirocyclic compounds have always attracted attention due to their presence as a structural core in a wide variety of natural and bioactive molecules and to exhibit pharmaceutical properties. An asymmetric synthesis of spiro[indoline‐3,4′‐pyrano[2,3‐c]pyrazoles] via Michael addition of trifluoromethyl substituted pyrazolone to isatylidene ethyl cyanoacetate derivatives was conducted with excellent enantioselectivities up to 99 % and up to 97 % isolated yield at room temperature with using 2 mol % of bifunctional quinine derived squaramide organocatalysts.

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“…[16] The catalysts devel-oped in our research group gave outstanding results in a wide variety of asymmetric transformation-type reactions. [14,17]…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of Trifluoromethyl Substituted Spiro[Indoline‐3,4′‐Pyrano[2,3‐c]Pyrazole] Derivatives with Organocatalysts

Özcan,

Kömüşdoğan,

Şahin

et al. 2024

ChemistrySelect

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Padlocking dihydrofurannulation for the control of small degree of helicity built on a fused-tetracyclic core

Gaucherand,

Yen-Pon,

García-López

et al. 2024

Chem. Sci.

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Novel transition metal-free synthetic protocols toward the construction of 2,3-dihydrobenzofurans: a recent update

Mushtaq,

Irfan,

Haq

et al. 2024

Front. Chem.

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2,3-Dihydrobenzofurans are noteworthy scaffolds in organic and medicinal chemistry, constituting the structural framework of many of the varied medicinally active organic compounds. Moreover, a diverse variety of biologically potent natural products also contain this heterocyclic nucleus. Reflecting on the wide biological substantiality of dihydrobenzofurans, several innovative and facile synthetic developments are evolving to achieve these heterocycles. This review summarizes the transition-metal-free, efficient, and novel synthetic pathways toward constructing the dihydrobenzofuran nucleus established after 2020.

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Organocatalytic enantioselective synthesis of dihydronaphthofurans and dihydrobenzofurans: reaction development and insights into stereoselectivity

Abstract: Squaramide/Cinchona alkaloid-derived bifunctional organocatalysts are highly in demand in asymmetric transformations. In this manner, bifunctional quinine-derived sterically encumbered squaramide (H-bond donor) organocatalysts were used to catalyze the asymmetric Friedel-Crafts/SN2 type...

Cited by 3 publications

References 43 publications

Asymmetric Synthesis of Trifluoromethyl Substituted Spiro[Indoline‐3,4′‐Pyrano[2,3‐c]Pyrazole] Derivatives with Organocatalysts

Asymmetric Synthesis of Trifluoromethyl Substituted Spiro[Indoline‐3,4′‐Pyrano[2,3‐c]Pyrazole] Derivatives with Organocatalysts

Padlocking dihydrofurannulation for the control of small degree of helicity built on a fused-tetracyclic core

Novel transition metal-free synthetic protocols toward the construction of 2,3-dihydrobenzofurans: a recent update

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