Chemistry Letters

A new finding in the Dieckmann type annulation of a chiral half-thiol diester having latent σ-symmetry

Y Nagao, T Nakamura, M Ochiai, K Fuji, E Fujita

Index: Nagao, Yoshimitsu; Nakamura, Takeshi; Ochiai, Masahito; Fuji, Kaoru; Fujita, Eiichi Chemistry Letters, 1987 , p. 1861 - 1864

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Abstract

It was revealed that the Dieckmann type annulation of a half-thiol diester having latent σ- symmetry did not always proceed in the regiocontrolled fashion even though the reaction yielded the desired β-keto ester. Direction of the regioselectivity dramatically differed depending on the base employed, which was demonstrated by treating an optically pure half- thiol diester with lithium diisopropylamide, dimsylsodium, and dimsylpotassium, ...