Asymmetric Diastereoselective Conjugate Additions of Lithium Amides to Chiral Naphthyloxazolines Leading to Novel β-Amino Acids

Article abstract of DOI:10.1021/jo00128a016

The functionalization of the naphthalene ring system by a direct amination-alkylation reaction of chiral nonracemic naphthyloxazolines is described.Chiral 1-naphthyl- and 2-naphthyloxazoline were treated with a variety of lithium amides followed by several different electrophilic quenches.The solvent and additives were varied in order to achieve optimum conditions.The combination of HMPA and THF at -78 deg C gave the best yield with excellent stereoselectivity.The present methology provides a stereospecific synthesis of novel, nonracemic, rigid β-amino acides after hydrolytic removal of the chiral oxazoline.