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  • Title: Mechanism of the regio- and diastereoselective ring expansion reaction using trimethylsilyldiazomethane.
    Author: Sakai T, Ito S, Furuta H, Kawahara Y, Mori Y.
    Journal: Org Lett; 2012 Sep 07; 14(17):4564-7. PubMed ID: 22900546.
    Abstract:
    An equatorial attack of TMS-diazomethane was determined to be the first step of the BF(3)-promoted ring expansion reaction of six-membered ketones using TMS-diazomethane. The migration reaction occurred in a conformation in which the carbonyl oxygen and the TMS group were antiperiplanar to predominantly afford trans-seven-membered ketones.
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