Stereoselective synthesis of (2E, 4E)-and (2Z, 4E)-2, 4-alkadienoates by the ester enolate Claisen rearrangement of (E)-1-alkyl-3-trimethylsilyl-2-propenyl glycolates …

T Sato, H Tsunekawa, H Kohama, T Fujisawa

Index: Sato, Toshio; Tsunekawa, Hiroshi; Kohama, Hiromasa; Fujisawa, Tamotsu Chemistry Letters, 1986 , p. 1553 - 1556

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Citation Number: 14

Abstract

The ester enolate Claisen rearrangement of (E)-1-alkyl-3-trimethylsilyl-2-propenyl glycolates gave (E)-erythro-2-hydroxy-3-trimethylsilyl-4-alkenoates with high diastereoselectivity, which were stereoselectively converted into (2E, 4E)-and (2Z, 4E)-2, 4-alkadienoates by the Peterson reaction.