Microwave-mediated palladium-catalyzed asymmetric allylic alkylation using chiral β-seleno amides

European Journal of Organic Chemistry

Volumn , Issue 22, 2006, Pages 4993-4997

  Braga, Antonio L ^a   Vargas, Fabrício ^a   Sehnem, Jasquer A ^a   Wessjohann, Ludger A ^b  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

Allylic alkylation; Microwave; Palladium; Selenium

Indexed keywords

EID: 33751316781     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600707     Document Type: Article

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49. + 370.0680, found 370.0677.
50. 2 (2.5 mol-%) were dissolved in appropriated solvent (3.6 mL). The solution was stirred under argon for 30 min. Bis(trimethylsilyl)acetamide (5.2 mmol) and 1,3-diphenyl-2-propenyl acetate (3) (1.73 mmol) were transferred with 3.6 mL of appropriated solvent to the reaction solution. A portion (0.35 mmol, 2 mL for each sample, total volume 9.90 mL) of this solution was transferred to a thick-walled Pyrex tube, KOAc (0.6 mmol) and the respective malonate 4a-d (0.630 mmol) were added and the reaction vessel was sealed with a silicon septum under nitrogen. The tube was positioned in a MicroWell 10 single mode cavity microwave from Personal Chemistry AB. Sweden, producing continuous irradiation at 2.45 GHz, and the sample was irradiated with suitable power for an appropriate time (Table 1). The solvent was removed and the crude product 5a-d was flash chromatographed on silica with hexane/ethyl acetate (99:1).