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High Chelation Control of Three Contiguous Stereogenic Centers in the Reformatsky Reactions of Indium Enolates with α-Hydroxy Ketones: Unexpected Stereochemistry of Lactone Formation

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

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamada-oka, Suita, Osaka 565-0871, Japan, Email:

S. A. Babu, M. Yasuda, Y. Okabe, I. Shibata, A. Baba, Org. Lett., 2006, 8, 3029-3032.

DOI: 10.1021/ol060943m

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The Reformatsky reaction of α-hydroxy ketones with indium enolates furnished highly diastereoselective lactones, while α-alkoxy ketones gave acyclic esters in moderate selectivities. A boat-type of chelated bicyclic transition state involving highly diastereoselective construction of three contiguous stereogenic centers is proposed.

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reaction pathway

Key Words

Lactones, Reformatsky Reaction

ID: J54-Y2006-1890