The Journal of Organic Chemistry

Asymmetric synthesis of 4, 4-disubstituted 1-naphthalenones. Diastereoselectivity as a function of metal alkoxides

T Wuensch, AI Meyers

Index: Wuensch, Thomas; Meyers, A. I. Journal of Organic Chemistry, 1990 , vol. 55, # 14 p. 4233 - 4235

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Citation Number: 20

Abstract

Summary: Chiral tricyclic lactam (5) was sequentionally metalated (LDA or LDA/zirconocene halides) and alkylated to give quaternary alkylation products (8) in 6-54: l diastereomeric ratio. Reduction and hydrolysis furnish the title compound in three steps with> 99% enantiomeric purity.