Palladium(0)-catalyzed cyclization reaction of polymer-supported aryl iodides with 1,2-allenyl carboxylic acids. A facile solid-phase synthesis of butenolides

Organic Letters

Volumn 2, Issue 10, 2000, Pages 1419-1422

  Ma, Shengming ^a   Duan, Dehui ^a   Shi, Zhangjie ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BUTENOLIDE; CARBOXYLIC ACID; DRUG DERIVATIVE; FURAN DERIVATIVE; GAMMA BUTYROLACTONE; IODIDE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

4-BUTYROLACTONE; ALKENES; CARBOXYLIC ACIDS; CATALYSIS; DRUG DESIGN; FURANS; IODIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PALLADIUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034682141     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0057481     Document Type: Article

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36. 2 (2 mL, 0.3 M, 0.6 mmol) was added and the mixture was stirred for an additional 30 min at the same temperature. The resin was filtered and washed with EtOAc. The filtrate was transferred to a separatory funnel and washed with 0.5 N HCl twice, and the aqueous layer was extracted with EtOAc. The combined extracts were dried and evaporated to give product 6aa (30 mg, 99% overall yield from Merrified resin based on the maximum loading of aryl iodide and 93% purity).
37. -1.
38. 2O (5 mL × 3), DMF (5 mL × 2), THF (5 mL × 3), and MeOH (10 mL × 3) and then dried under high vacuum overnight to afford resin 5aa (101 mg, ∼100% overall yield from Merrified resin based on the maximum loading of aryl iodide).
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40. 3, 5% HCl, and a saturated aqueous NaCl solution. The organic layer was dried, filtered, and concentrated to afford product 6ca (42 mg, 89% overall yield from Merrified resin and 94% purity).