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Top Curr Chem. 2014;346:163-93. doi: 10.1007/128_2013_505.

Asymmetric transformations via C-C bond cleavage.

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  • 1Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, School of Basic Sciences, Ecole Polytechnic Fédérale de Lausanne, 1015, Lausanne, Switzerland.


Catalytic asymmetric transformations operating by carbon-carbon (C-C) bonds cleavages have emerged as intriguing strategies to access transient organometallic species from different reaction pathways. The reactions and the applicable substrate range have expanded considerably over the last decade. This overview covers the main developments in this field. A major focus is placed on β-carbon eliminations of strained tert-alcohols and related processes which have been shown to be particularly versatile in a broad range of transformations. Furthermore, exciting developments of asymmetric processes based on direct oxidative C-C bond insertion reactions, for instance into the acyl C-C bond of ketones or the C-CN bond of nitriles, are discussed.

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