The reaction of 1-(
![](/images/gifchars/alpha.gif)
-aminoalkyl)-2-diphenylphosphinoferrocene (
1) with glyoxals gave via an unusual heterocyclization 1,2-ferrocenediylazaphosphinines(
3) as a new class of planar-chiral ferrocenes. Theproducts were fully characterized by analytical
andvarious spectroscopic techniques. In particular, a complete assignment of all protons
and carbons was madeby various NMR techniques. A substantial degree of
![](/images/gifchars/pi.gif)
-electron delocalization extending over the fused heterocyclic ring can be evidenced by IR
and UV/vis spectra
and in the case of
3a by X-ray crystallographic data.Employment of
rac-3a as lig
and for Cu-catalyzed cyclopropanation of styrene by ethyl diazoacetate revealed acomplete diastereo-discrimination leading to the formation of
trans-product in 100% yield.