Journal of Organic Chemistry p. 7445 - 7455 (1995)
Update date:2022-08-28
Topics:
Shimano, Masanao
Meyers, A. I.
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.
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