Stereocontrolled synthesis of tertiary silanes via optically pure 1,3,2-oxazasilolidine derivatives

Optically pure 1,3,2-oxazasilolidine derivatives were synthesized from a chiral 1,2-amino alcohol. These heterocyclic compounds containing a stereogenic silicon atom produced tertiary silanes with excellent optical purity through successive reactions with Grignard reagents and diisobutylaluminum hydride. Stereochemical course of the reactions of the oxazasilolidine at the chiral silicon atom was elucidated based on the absolute configurations of the products and the substrate which were determined by chiral HPLC and X-ray crystallographic analyses.

Graphical abstractOptically pure 1,3,2-oxazasilolidine derivatives were synthesized from chiral 1,2-amino alcohols. The oxazasilolidine derivatives afforded tertiary silanes with excellent optical purity through successive reactions with Grignard reagents and DIBAL. Stereochemical course of the reactions was determined based on an X-ray crystallographic analysis.Figure optionsDownload full-size imageDownload as PowerPoint slide