Alkylation of δ-ketoesters : a mechanism change depending on conformational mobility and substituent effects on stereoselection.

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Abstract

Kinetic evidence shows that the two groups of a δ-ketoester can interact in the transition state of a Grignard reaction. This promotes high stereoselectivity by chiral center far from the ketonic group and produces good correlations between stereoselection and electronic effects of substituents. © 1982.

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Di Maio, D., Vecchi, E., & Zeuli, E. (1982). Alkylation of δ-ketoesters : a mechanism change depending on conformational mobility and substituent effects on stereoselection. Tetrahedron Letters, 23(49), 5211–5214. https://doi.org/10.1016/S0040-4039(00)85800-1

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