Synthesis of. beta.,. gamma.-unsaturated esters. Direct generation of ester dienolates from. beta.-keto ester tosylhydrazone trianions

CA Bunnell, PL Fuchs

Index: Bunnell,C.A.; Fuchs,P.L. Journal of the American Chemical Society, 1977 , vol. 99, # 15 p. 5184 - 5187

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Citation Number: 20

Abstract

The chlorine atom in la should enhance the acidity of the proton at C-7 and accelerate the metalation reacti~ n'~.'~ to 4. The consecutive/3 elimination of lithium chloride from 4 leads to tricyclo [4.1. 0.02 v7] hept-1 (7)-ene (5) as a reaction intermediate. This highly strained hydrocarbon adds, as expected, the organolithium reagent with the formation of