Tetrahedron: Asymmetry

Stereoselective construction of quaternary carbon centers. Synthesis of optically active γ, γ-disubstituted γ-butyrolactones.

R Bloch, B Cécile

Index: Bloch, Robert; Brillet, Cecile Tetrahedron: Asymmetry, 1991 , vol. 2, # 8 p. 797 - 800

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Citation Number: 14

Abstract

Abstract An unusually strong solvent effect has been observed on the diastereoselectivity of nucleophilic additions of bromoalkylmagnesium compounds to the lactols 2 and 3, allowing the formation of pure diastereoisomers of 1, 4-diols. Homochiral γ, γ-disubstituted γ- butyrolactones could then be obtained after oxidation of these dials followed by a retro Diels- Alder reaction as illustrated by the synthesis of S-(+)-4, 5-dimethyl-4-hexanolide.