Optically Active Phospholes: Synthesis and Use as Chiral Precursors for Phosphinidene and Phosphaferrocene Complexes

Phospholes bearing chiral menthyl, myrtanyl, and (4-isopropyloxazolino)phenyl groups at the phosphorus atom were prepared. They were used as precursors for 7-phosphanorbornadienes and phosphinidene complexes. Unexpectedly, the [(4-isopropyloxazolino)phenyl]phosphinidene gave an intramolecular adduct with the imine moiety, which behaved as a 1,3-dipole in cycloaddition reactions. This afforded a new, general approach to 7-aza-1-phosphanorbornadiene and norbornene derivatives. The (4-isopropyloxazolino)phenyl-substituted phosphole was also used for the synthesis of new chiral phosphaferrocene complexes bearing oxazoline moieties. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)