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Mechanistic identification and improvement of a direct enantioconvergent transformation in copper-catalyzed asymmetric allylic alkylation

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Published in Chemical Science. 2012, vol. 3, no. 4, p. 1062
Abstract Recently, our group reported on the development of an unprecedented process in copper-catalyzed Asymmetric Allylic Alkylation. This method allowed for the quantitative transformation of a racemic substrate into an enantioenriched product. While a high level of asymmetric induction (up to 99% ee) was observed, the mechanistic understanding of the reaction remained fuzzy. In the present article, a thorough mechanistic analysis, based on computational investigations, led to the identification of the reaction pathway. Notably, it uncovered that both enantiomers of the starting material converged independently to the same product via two different mechanistic routes. This specific feature established this process as a rare example of Direct Enantioconvergent Transformation. Finally, the modelling results prompted a valuable improvement of the reaction, relying on the use of a more accessible range of substrates.
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Other version: http://xlink.rsc.org/?DOI=c2sc00868h
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LANGLOIS, Jean-Baptiste et al. Mechanistic identification and improvement of a direct enantioconvergent transformation in copper-catalyzed asymmetric allylic alkylation. In: Chemical Science, 2012, vol. 3, n° 4, p. 1062. https://archive-ouverte.unige.ch/unige:18777

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Deposited on : 2012-03-09

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