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Palladium-Catalyzed Asymmetric Allylic Alkylation in the Presence of Chiral Cinchonidinium Salts
Palladium-Catalyzed Asymmetric Allylic Alkylation in the Presence of Chiral Cinchonidinium Salts
Journal of the Korean Chemical Society. 2008. Dec, 52(6): 724-726
Copyright © 2008, The Korean Chemical Society
  • Received : October 02, 2008
  • Published : December 20, 2008
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주양 맹
일선 황
대길 권
대영 김

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EXPERIMENTAL
- General procedure for the Pd-catalyzed enantioselective allylic alkylation of malonates 2
To a solution of [Pd(η 3 -C 3 H 5 )Cl] 2 (0.9 mg, 0.0025 mmol), n -tributyl phosphine (1 mL, 0.005 mmol), and rac -1,3-diphenyl-2-enyl acetate ( 1 , 25.2 mg, 0.1 mmol) in mesitylene (0.5 mL) were successively added Rb 2 CO 3 (184.7 mg, 0.8 mmol), chiral ammonium salt VIII (6.1 mg, 0.01 mmol), and malonate (2, 0.2 mmol) at room temperature. After being stirred vigorously for 48 h, the reaction mixture was diluted with ethyl acetate (20 mL). The organic phase was washed with water (2 × 10 mL) and brine (10 mL). The extract was dried over MgSO 4 , filtered, and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, ethyl acetate : benzene : hexane = 1:1:12) to give alkylated products 3 .
Acknowledgements
This research was financially supported by the Ministry of Education, Science, Technology (MEST) and Korea Industrial Technology Foundation (KOTEF) through the Human Resource Training Project for Regional Innovation.
References
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