Organic Chemistry Portal



Zinc Carbenoid-Mediated Chain Extension: Preparation of α,β-Unsaturated-γ-keto Esters and Amides

Matthew D. Ronsheim and Charles K. Zercher*

*Department of Chemistry, University of New Hampshire, Durham, New Hampshire 03824, Email:

M. D. Ronsheim, C. K Zercher, J. Org. Chem., 2003, 68, 4535-4538.

DOI: 10.1021/jo026299g


A zinc carbenoid-mediated chain extension of β-dicarbonyl compounds provides access to α,β-unsaturated-γ-keto esters and amides with complete E selectivity via an intermediate zinc enolate, which is treated sequentially with iodine and DBU.

see article for more examples

Formation of β-Substituted γ-Keto Esters via Zinc Carbenoid Mediated Chain Extension

W. Lin, R. J. McGinness, E. C. Wilson, C. K. Zercher, Synthesis, 2007, 2404-2408.

Key Words

chain extension, oxidation, elimination, iodine, α,β-unsaturated esters

ID: J42-Y2003-240