Diastereoselective alkylation and aldol reactions mediated by the D-mannitol-derived oxazolidin-2-one as a chiral auxiliary

摘要

Chiral N-acylated oxazolidin-2-ones readily available from D-mannitol have been demonstrated to undergo highly diastereoselective alkylation reactions via their lithium imide Z-enolates to afford a-branched products. Evans syn and non-Evans syn aldol products were also selectively obtained using this new auxiliary in high diastereomeric purity by simply changing the stoichiometry of TiCl4 and the nature of the amine base. [References: 27]