Gold‐Catalyzed Asymmetric Transformation of Hydroxylated Propargylic Esters DOI
Carlos D. Quintanilla, Ke Zhao, Liming Zhang

et al.

ChemPlusChem, Journal Year: 2023, Volume and Issue: 88(10)

Published: Aug. 7, 2023

By combining tandem asymmetric gold catalysis and subsequent stereoconvergent hydrolysis of enol ester in a one-pot process, hydroxylated propargylic esters are converted into chiral β-oxygenated ketones with mostly good enantiomeric ratios largely to excellent yields. The product center is formed via stereoselective cyclization allenyl intermediate, which enabled by gold-ligand cooperation.

Language: Английский

Gold(I)-Catalyzed Rautenstrauch/Hetero-Diels–Alder/Retro-aza-Michael Cascade Reaction for the Synthesis of α-Hydrazineyl-2-cyclopentenones DOI
Dina Scarpi,

Claudia Capanni,

Samuele Visi

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 12, 2024

A one-pot synthesis of ring-fused, α-hydrazineyl-2-cyclopentenone derivatives is achieved by a gold(I)-catalyzed Rautenstrauch/hetero Diels-Alder/ring opening tandem reaction suitable propargyl esters. By mixing the latter with dialkylazodicarboxylate in presence gold(I) catalyst, 1,2-acyloxy migration/cyclization process (Rautenstrauch reaction) leads to cyclopentadienyl ester intermediates which are trapped heterodienophile present situ. This provides strained spontaneously undergo highly regioselective ring retro aza-Michael promoted eventually yielding target compounds. Six- and seven-membered ring-fused cyclopentenones bearing pendant α-hydrazineyl moiety can be obtained moderate excellent yield (50-98%) this approach, minimal erosion initial optical purity when using enantioenriched substrates.

Language: Английский

Citations

0
Gold(I)-Catalyzed Reactions of exo-Glycals with Propargyl Esters toward C-1 Alkenyl Spirocyclopropyl Carbohydrates DOI
Mylène Lang,

S. Walter,

Delphine Hatey

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(38), P. 8017 - 8022

Published: Sept. 16, 2024

An atom-economic and diazo-free strategy for the construction of novel pseudo anomeric C-1 alkenyl spirocyclopropyl sugars is described. Leveraging 1,2-migration pathway propargyl esters under gold(I) catalysis, easily available

Language: Английский

Citations

0
Gold(I)-Catalyzed 6-exo-dig Hydroamination/7-endo-dig Cycloisomerization Domino Approach to 3,7a-Diazacyclohepta[jk]fluorene Derivatives DOI
Yang Lu,

Fukai Xie,

Lianjie Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 10030 - 10035

Published: Nov. 14, 2024

A series of 3,7

Citations

0
Gold/HNTf2-Cocatalyzed Asymmetric Annulation of Diazo-Alkynes: Divergent Construction of Atropisomeric Biaryls and Arylquinones DOI
Yibo Wang, Wei Liu, Ting Li

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 30, 2024

Due to the inherent challenges posed by linear coordination of gold(I) complexes, asymmetric gold-catalyzed processes remain challenging, particularly in atroposelective synthesis axially chiral skeletons. Except for extremely few examples intramolecular annulations, construction axial chirality via intermolecular alkyne transformation is still undeveloped. Herein, a gold/HNTf

Language: Английский

Citations

0
Gold‐Catalyzed Asymmetric Transformation of Hydroxylated Propargylic Esters DOI
Carlos D. Quintanilla, Ke Zhao, Liming Zhang

et al.

ChemPlusChem, Journal Year: 2023, Volume and Issue: 88(10)

Published: Aug. 7, 2023

By combining tandem asymmetric gold catalysis and subsequent stereoconvergent hydrolysis of enol ester in a one-pot process, hydroxylated propargylic esters are converted into chiral β-oxygenated ketones with mostly good enantiomeric ratios largely to excellent yields. The product center is formed via stereoselective cyclization allenyl intermediate, which enabled by gold-ligand cooperation.

Language: Английский

Citations

1