Gold(I)-Catalyzed Tandem Intramolecular Methoxylation/Double Aldol Condensation Strategy Yielding 2,2′-Spirobi[indene] Derivatives

Zhang, Jingfu; Zhang, Sen; Ding, Zhixing; Hou, Anbin; Fu, Jiayue; Su, Hongwei; Cheng, Maosheng; Lin, Bin; Yang, Lu; Liu, Yongxiang

doi:10.1021/acs.orglett.2c02653

Cited by 5 publications

(2 citation statements)

References 64 publications

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“…The ketene units of 124 were then attacked by nucleophiles (ROH) to form enol intermediates (125). Activation of a triple bond by gold(I) species initiated a C-5-endo- Recently, the Liu group developed a synthetic strategy for 2,2 -spirobi[indene] derivatives using arylalkyne-acetal substrates based on their previous research (Schemes 22 and 24), mainly involving methoxylation and aldol condensation (Scheme 25) [58]. Intermediates (120) were easily produced by the activation of [Au] + /H + and converted into intermediates (121) through an intramolecular aldol reaction.…”

Section: Other Arylalkyne Substratesmentioning

confidence: 99%

Recent Advances in Gold(I)-Catalyzed Approaches to Three-Type Small-Molecule Scaffolds via Arylalkyne Activation

Yang

Sun

et al. 2022

Molecules

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Gold catalysts possess the advantages of water and oxygen resistance, with the possibility of catalyzing many novel chemical transformations, especially in the syntheses of small-molecule skeletons, in addition to achieving the rapid construction of multiple chemical bonds and ring systems in one step. In this feature paper, we summarize recent advances in the construction of small-molecule scaffolds, such as benzene, cyclopentene, furan, and pyran, based on gold-catalyzed cyclization of arylalkyne derivatives within the last decade. We hope that this review will serve as a useful reference for chemists to apply gold-catalyzed strategies to the syntheses of related natural products and active molecules, hopefully providing useful guidance for the exploration of additional novel gold-catalyzed approaches.

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Section: Other Arylalkyne Substratesmentioning

confidence: 99%

Recent Advances in Gold(I)-Catalyzed Approaches to Three-Type Small-Molecule Scaffolds via Arylalkyne Activation

Yang

Sun

et al. 2022

Molecules

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“…This method covers a wide scope of substrates and provides excellent enantiomeric excesses (up to 88%). The alternative strategy involves gold(I)-catalyzed tandem intramolecular methoxylation/double aldol condensation 20 (Scheme 1, e). Despite giving excellent yields, this method requires complicated substrates and cannot produce enantiopure spirocycles.…”

Section: ■ Introductionmentioning

confidence: 99%

Construction of Annulated Spiro[4.4]-nonane-diones via the Tandem [4 + 2]-Cycloaddition/Aromatization Reaction

Ivanov,

Samburskiy,

Zargarova

et al. 2023

J. Org. Chem.

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A method for the synthesis of both symmetric and asymmetric fused spiro[4.4]-nonane-dione derivatives has been developed. It is based on a Diels–Alder reaction of spiro[4.4]nona-2,7-diene-1,6-dione as a dienophile component followed by immediate aromatization of the adduct. An active diene component can be generated using the tetrabromoxylene/NaI system, the 1,3-diphenylisobenzofuran/BF3 system, or substituted cyclones.

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Gold(I)-Catalyzed 6-exo-dig Hydroamination/7-endo-dig Cycloisomerization Domino Approach to 3,7a-Diazacyclohepta[jk]fluorene Derivatives

Yang,

Xie,

Zhang

et al. 2024

Org. Lett.

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Gold(I)-Catalyzed Tandem Intramolecular Methoxylation/Double Aldol Condensation Strategy Yielding 2,2′-Spirobi[indene] Derivatives

Cited by 5 publications

References 64 publications

Recent Advances in Gold(I)-Catalyzed Approaches to Three-Type Small-Molecule Scaffolds via Arylalkyne Activation

Recent Advances in Gold(I)-Catalyzed Approaches to Three-Type Small-Molecule Scaffolds via Arylalkyne Activation

Construction of Annulated Spiro[4.4]-nonane-diones via the Tandem [4 + 2]-Cycloaddition/Aromatization Reaction

Gold(I)-Catalyzed 6-exo-dig Hydroamination/7-endo-dig Cycloisomerization Domino Approach to 3,7a-Diazacyclohepta[jk]fluorene Derivatives

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