Stereoselectivity in the 1,4-addition reaction of organocopper reagents to ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]propenoate

Add time:07/18/2019    Source:sciencedirect.com

The chemo- and stereoselectivity in reactions with E and Z isomers of ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate, 1 and 2, are strongly dependent on the composition of the organocopper reagent. Synthetically useful yields and stereoselectivities are obtained with reagents of good nucleophilicity, e. g. RCu-TMSI-LiI. A transition state model based on copper-alkene π-complex formation with intramolecular chelation of the γ-oxygen to lithium of a copper-lithium cluster can be used to rationalize the observed anti selectivity.

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