DIASTEREOSELECTIVE ALKYLATION AND ALDOL REACTIONS MEDIATED BY THE d-MANNITOL-DERIVED OXAZOLIDIN-2-ONE AS A CHIRAL AUXILIARY

ABSTRACT

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 α-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.

Keywords:

• Oxazolidin-2-one
• d-mannitol
• Alkylation
• Aldol reaction

ACKNOWLEDGMENT

This research was supported by the Hallym Academy of Sciences at Hallym University, Korea, 2001.