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Zinc-Mediated Ring-Expansion and Chain-Extension Reactions of β-Keto Esters

Song Xue,* Yong-Kang Liu, Le-Zhen Li and Qing-Xiang Guo

*Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China, Email:

S. Xue, Y.-K. Liu, L.-Z. Li, Q.-X. Guo, J. Org. Chem., 2005, 70, 8245-8247.

DOI: 10.1021/jo0512498


The reaction of β-keto esters with CF3CO2ZnCH2I provided the corresponding chain-extended products in moderate to good yields. α-Substituted acyclic β-keto esters reacted less efficiently than cyclic β-keto esters or simple β-keto esters.

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proposed mechanism

Zinc-Mediated Chain Extension Reaction of 1,3-Diketones to 1,4-Diketones and Diastereoselective Synthesis of trans-1,2-Disubstituted Cyclopropanols

S. Xue, L.-Z. Li, Y.-K. Liu, Q.-X. Guo, J. Org. Chem., 2006, 71, 215-218.

DOI: 10.1021/jo051950b

Key Words

Chain-Extension, Ring Expansion, Cyclopentanones

ID: J42-Y2005-1520