103539-06-6Relevant articles and documents
SIGMATROPIC REARRANGEMENT OF ALLYLIC ALCOHOLS WITH ETHYL β,β-DIETHOXYACRYLATE: REGIOSPECIFIC SYNTHESIS OF SUBSTITUTED ALLYLMALONATES.
Raucher, Stanley,Chi, Ki-Whan,Jones, David S.
, p. 6261 - 6264 (1985)
Sigmatropic rearrangement of allylic alcohols with ethyl β,β-diethoxyacrylate provides a convenient method for the regiospecific synthesis of substituted allylmalonates 3.
On the Regio- and Stereoselectivity of Bu4N-Catalyzed Allylic Alkylation
Xu, Yuanyao,Zhou, Bo
, p. 974 - 977 (1987)
Bu4N has been found to catalyze the alkylation of allylic carbonate with malonate anion.The reaction proceeds with good regioselectivity, the nucleophile attacking predominantly at the carbon where the leaving group was attached.Retention of configuration of the double bond during the course of reaction was observed.Alkylation of methyl (Z)-5-carbomethoxy-1-cyclohexen-3-yl carbonate with sodium salt of dimethyl malonate yielded dimethyl ((Z)-5-carbomethoxy-1-cyclohexen-3-yl)malonate in a highly stereoselective fashion, and a net retention of configuration at the center undergoing substitution is thus established.On the basis of regio- and stereochemical results, a reaction pathway involving an ?-allyliron complex has been suggested.
