Pd(II)/Pd(IV) catalytic enantioselective synthesis of bicyclo[3.1.0]hexanes via oxidative cyclization of enynes

Pd(II)/Pd(IV) catalytic enantioselective synthesis of bicyclo[3.1.0]hexanes via oxidative cyclization of enynes

The first asymmetric Pd(II)/Pd(IV) catalysis has been achieved by employing the combination of a hypervalent iodine reagent and a chiral ligand, SPRIX. Enantioselective cyclization of enyne derivatives catalyzed by the Pd-i-Pr-SPRIX complex furnished lactones bearing a bicyclo[3.1.0]hexane skeleton...

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Veröffentlicht in:Journal of the American Chemical Society 2009-03, Vol.131 (10), p.3452-3453
Hauptverfasser: Tsujihara, Tetsuya, Takenaka, Kazuhiro, Onitsuka, Kiyotaka, Hatanaka, Minoru, Sasai, Hiroaki
Format: Artikel
Sprache:eng
Schlagworte:
Bridged Bicyclo Compounds - chemical synthesis
Catalysis
Cyclization
Oxidation-Reduction
Palladium - chemistry
Stereoisomerism
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Zusammenfassung:The first asymmetric Pd(II)/Pd(IV) catalysis has been achieved by employing the combination of a hypervalent iodine reagent and a chiral ligand, SPRIX. Enantioselective cyclization of enyne derivatives catalyzed by the Pd-i-Pr-SPRIX complex furnished lactones bearing a bicyclo[3.1.0]hexane skeleton with up to 95% ee.
ISSN:1520-5126
DOI:10.1021/ja809965e