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Letter

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

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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

Org. Lett., 2006, 8 (14), pp 3029–3032

DOI: 10.1021/ol060943m

Publication Date (Web): June 16, 2006

†

Present address: Research Center for Environmental Preservation.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, baba@chem.eng.osaka-u.ac.jp

Abstract

A boat-type of chelated bicyclic transition state involving highly diastereoselective construction of three contiguous stereogenic centers in the Reformatsky reaction of indium enolates with α-alkoxy/hydroxy ketones is proposed. α-Hydroxy ketones with indium enolates furnished highly diastereoselective lactones, while α-alkoxy ketones gave acyclic esters in moderate selectivities. X-ray structure analyses of key products unequivocally revealed the unexpected stereochemistry of products and the reaction pathway.

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Published In Issue July 06, 2006
Received April 19, 2006

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Letter

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

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

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

Total Synthesis of (−)-Acutumine

A Simple and Efficient Procedure of Low Valent Iron- or Copper-Mediated Reformatsky Reaction of Aldehydes

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