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Synlett 1999; 1999(4): 405-408
DOI: 10.1055/s-1999-2623
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Lewis Acid Mediated Diastereoselective Allylation of 3-Menthyloxycarbonyl-5,6-dihydropyridin-4-ones

Sylvie Brocherieux-Lanoy* , Hamid Dhimane, Corinne Vanucci-Bacqué, Gérard Lhommet
  • *Université Pierre et Marie Curie, Laboratoire de Chimie des Hétérocycles, UMR 7611, 4 Place Jussieu, F-75252 Paris Cedex 05, France; Fax 33(0)1 44 27 30 56; E-mail: lhommet@ccr.jussieu.fr
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Publikationsdatum:
31. Dezember 1999 (online)

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Sakurai allylation of menthyl enoates 5a-c afforded adducts 7a-c with low to excellent facial selectivity, depending on the Lewis acid employed to promote this 1,4-nucleophilic addition of allyltrimethylsilane. A chelated model was assumed to explain the observed diastereoselectivity.

Sakurai allylation - dihydropyridone - stereoselective - Lewis acid - chiral auxiliaries

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