Novel [1,2]- and [2,3]-Wittig Rearrangements of α-Benzyloxy β-CF3-β-lactam Enolates

α-Benzyloxy α-CF3-β-lactams are shown to offer the first examples of the enolate [1,2]- and enolate ortho-[2,3]-Wittig rearrangements which provide a unique entry to the α-benzyl-α-hydroxy lactams and the α-aryl-α-hydroxy lactams, respectively. Both products are potential precursors of new trifluoro...

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Veröffentlicht in:Organic letters 2001-08, Vol.3 (16), p.2529-2531
Hauptverfasser: Garbi, Amel, Allain, Lydie, Chorki, Fatima, Ourévitch, Michèle, Crousse, Benoît, Bonnet-Delpon, Danièle, Nakai, Takeshi, Bégué, Jean-Pierre
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Sprache:eng
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Zusammenfassung:α-Benzyloxy α-CF3-β-lactams are shown to offer the first examples of the enolate [1,2]- and enolate ortho-[2,3]-Wittig rearrangements which provide a unique entry to the α-benzyl-α-hydroxy lactams and the α-aryl-α-hydroxy lactams, respectively. Both products are potential precursors of new trifluoromethyl isoserines, and the latter is not accessible via the usual alkylation methodology.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol016198p