Cu(I)-catalyzed highly exo-selective and enantioselective [3 + 2] cycloaddition of azomethine ylides with acrylates

Organic Letters

Volumn 7, Issue 19, 2005, Pages 4241-4244

  Gao, Wenzhong ^a   Zhang, Xumu ^a   Raghunath, Malati ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID BUTYL ESTER; ACRYLIC ACID DERIVATIVE; ALKENE; AZO COMPOUND; AZOMETHINE; COPPER; DRUG DERIVATIVE; GLYCINE; GLYCINE METHYL ESTER; LIGAND; N-BUTYL ACRYLATE; THIOSEMICARBAZONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ENZYME SPECIFICITY; STEREOISOMERISM;

ACRYLATES; ALKENES; AZO COMPOUNDS; CATALYSIS; COPPER; CYCLIZATION; GLYCINE; LIGANDS; MOLECULAR STRUCTURE; STEREOISOMERISM; SUBSTRATE SPECIFICITY; THIOSEMICARBAZONES;

EID: 25444439300     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0516925     Document Type: Article

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36. 4 (8.2 mg, 0.025 mmol, 5 mol %) and ligand L4 (15.1 mg, 0.0275 mmol, 5.5 mol %) in THF (2 mL) for 1 h at room temperature. The mixture was then cooled to -25°C, imine substrate 1 (0.50 mmol), dipolarophile 2 (0.75 mmol, 1.5 equiv), and base (0.05 mmol, 10 mol %) were added subsequently, and the resulting mixture was stirred at -25°C for 20 h. When the reaction was complete as monitored by TLC, the mixture was passed through a short column of silica gel and the diastereometric ratio (exo/endo) was determined by the NMR spectroscopic analysis of the crude product. The pure adducts were then purified by column chromatography on silica gel (hexanes/ethyl acetate/1% triethylamine).
37. CCDC-268934 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK.; fax: (+44)1223-336-033; or depost@ccdc.cam.ac.uk).