Asymmetric induction during carbonylation of an optically active organopalladium. A novel and versatile route to enantiomeric glycerides.

Article abstract of DOI:10.1016/0022-328X(85)87383-6

In the course of carbonylation of optically active [η⁵-C₅H₅Feη₅- CH₅H₃CH₂NMe₂PdCl]₂ (1) in prochiral diols, the asymmetric induction of a newly developed chiral centre by a chiral plane has been performed. For 2-O-benzyl- glycerol, the extent of asymmetric induction, that means diastereoselectivity, was found to be about 36%. The protection of a free hydroxyl followed by hydrolysis of a ferrocenoyl derivative resulted in enantiomeric 2-O-benzyl-3-O-trityl-sn-glycerol (4) which can serve as a key intermediate in the synthesis of optically active mono-, di- and tri-substituted glycerides. This methodology has been illustrated by the detailed description of the preparation of 1-palmitoyl-sn-glycerol.