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Stephanie Seel, Dr. Guillaume Dagousset, Dr. Tobias Thaler, Annette Frischmuth, Prof. Dr. Konstantin Karaghiosoff, Prof. Dr. Hendrik Zipse and Prof. Dr. Paul Knochel Preparation of Stereodefined Secondary Alkyllithium Compounds Chemistry - A European Journal 19

Version of Record online: 10 FEB 2013 | DOI: 10.1002/chem.201204076

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Love the way you Li/I: A stereoretentive iodine/lithium-exchange process allows the stereodefined preparation of cis- and trans-cycloalkyllithiums from their corresponding diastereomerically pure iodides. Quenching with electrophiles offers access to both cis- (up to 96 %) and trans-cycloalkyl derivatives (up to 99 %). The formation of oligomeric cyclohexyllithium structures was pivotal for explaining the observed stereochemical preference.

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