Novel [12]- and [2,3]-Wittig rearrangements of alpha-benzyloxy beta-CF3-beta-lactam enolates

Authors
Garbi, A Allain, L Chorki, F Ourevitch, M Crousse, B Bonnet-Delpon, D Nakai, T Begue, JP
Citation
A. Garbi et al., Novel [12]- and [2,3]-Wittig rearrangements of alpha-benzyloxy beta-CF3-beta-lactam enolates, ORG LETT, 3(16), 2001, pp. 2529-2531
Citations number
30
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
16
Year of publication
2001
Pages
2529 - 2531
Database
ISI
SICI code
1523-7060(20010809)3:16<2529:N[A[RO>2.0.ZU;2-G
Abstract
[GRAPHICS] alpha -Benzyloxy alpha -CF3-beta -lactams are shown to offer the first exam ples of the enolate [1,2]- and enolate ortho-[2,3]-Wittig rearrangements wh ich provide a unique entry to the alpha -benzyl-alpha -hydroxy lactams and the alpha -aryl-alpha -hydroxy lactams, respectively. Both products are pot ential precursors of new trifluoromethyl isoserines, and the latter is not accessible via the usual alkylation methodology.