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Evans–Tishchenko reaction
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Evans–Tishchenko reaction : ウィキペディア英語版
Evans–Tishchenko reaction
The Evans–Tishchenko reaction is the diastereoselective reduction of β-hydroxy ketones to the corresponding 1,3-''anti'' diol monoesters. The reaction employs a Lewis acid, often samarium iodide, and an aldehyde. It was first described in 1990 by David A. Evans and Amir Hoveyda, as a development of the well-known Tishchenko reaction discovered in 1906.
== Mechanism ==
The reaction mechanism involves the attack of the aldehyde from the free alcohol group. The Lewis acid can then chelate between the two oxygen atoms to form a cyclic, 6-membered transition state. The hydride, formerly the formyl hydrogen on the aldehyde, is delivered intramolecularly, accounting for the observed ''anti'' diastereoselectivity: the result is a 1,3-''anti'' diol monoester. The proposed mechanism is further supported by isotopic labeling, which demonstrates that the formyl hydrogen is the one that migrates.

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