Novel [1,2]- and [2,3]-Wittig rearrangements of alpha-benzyloxy beta-CF(3)-beta-lactam enolates.
[reaction: see text] alpha-Benzyloxy alpha-CF(3)-beta-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 alpha-benzyl-alpha-hydroxy lactams and the alpha-aryl-alpha-hydroxy lactams, respectively. Both products are potential precursors of new trifluoromethyl isoserines, and the latter is not accessible via the usual alkylation methodology.
Garbi
A
A
BIOCIS, Centre d'Etudes Pharmaceutiques, rue J.B. Clément, Châtenay-Malabry F-92296 Cedex, France.
Allain
L
L
Chorki
F
F
Ourévitch
M
M
Crousse
B
B
Bonnet-Delpon
D
D
Nakai
T
T
Bégué
J P
JP
D000478:Alkylation; D007202:Indicators and Reagents; D047090:beta-Lactams / Q000737:chemistry*
D007202:Indicators and Reagents; D047090:beta-Lactams