There are re
lative
ly few methods for the cata
lytic asymmetric synthesis of
le">-
lactams, and those that have been reported are genera
lly cis se
lective. This communication describes the first cata
lytic enantiose
lective Staudinger reactions that preferentia
lly furnish trans
le">-
lactams (trans = re
lationship of Ph to R
1). The key to this method is the use of an
N-trif
ly
l protecting group for the imine. A
long with serving as interesting targets in their own right,
N-trif
ly
l le">-
lactams readi
ly react with nuc
leophi
les to generate usefu
l fami
lies of compounds, such as
-amino a
lcoho
ls and
le">-amino acids.