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In- or In(I)-Employed Tailoring of the Stereogenic Centers in the Reformatsky-Type Reactions of Simple Ketones, α-Alkoxy Ketones, and β-Keto Esters

Srinivasarao Arulananda Babu, Makoto Yasuda, Ikuya Shibata and Akio Baba*

*Department of Applied Chemistry and Handai Frontier Research Center, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan, Email: babachem.eng.osaka-u.ac.jp

S. A. Babu, M. Yasuda, I. Shibata, A. Baba, J. Org. Chem., 2005, 70, 10408-10419.

DOI: 10.1021/jo051659w (free Supporting Information)


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Abstract

Efficient In- or In(I)-based diastereoselective Reformatsky-type reactions of simple ketones, α-alkoxy ketones, and β-keto esters were developed. High anti selectivity was established in the addition of the branched α-halo ester derivatives to simple ketones using indium metal under THF-refluxing conditions. Syn selective additions to α-alkoxy ketones and β-keto esters required either In(I)X or In-InCl3 systems in toluene under ultrasonication.

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Key Words

Reformatsky Reaction, β-Hydroxy Esters


ID: J48-Y2005-2110