Selective. gamma. alkylation of dienolate anions derived from. alpha.,. beta.-unsaturated acids. Applications to the synthesis of isoprenoid olefins

JA Katzenellenbogen, AL Crumrine

Index: Katzenellenbogen,J.A.; L Crumrine,A. Journal of the American Chemical Society, 1976 , vol. 98, # 16 p. 4925 - 4935

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Citation Number: 112

Abstract

Abstract: Lithium dienolates derived from a, fl-unsaturated carbonyl compounds generally undergo alkylation reactions nearly exclusively at the a (rather than the y) carbon. Changing the counterion from lithium to copper (I), however, has a remarkable effect on the alkylation regioselectivity of these dienolates. A systematic investigation has been made of the reaction of dienolates derived from (Z)-and (E)-3-methyl-2-hexenoic (2a and 3a) and ...