The Journal of Organic Chemistry

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

M Shimano, AI Meyers

Index: Shimano, Masanao; Meyers, A. I. Journal of Organic Chemistry, 1995 , vol. 60, # 23 p. 7445 - 7455

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Citation Number: 40

Abstract

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" C gave the best yield with excellent ...