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Royal Society of Chemistry, Chemical Science, 5(6), p. 2770-2776, 2015

DOI: 10.1039/c5sc00445d

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Remote functionalization of hydrocarbons with reversibility enhanced stereocontrol

Journal article published in 2015 by Alexandre Vasseur, Lionel Perrin ORCID, Odile Eisenstein ORCID, Ilan Marek
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

Remote functionalization of hydrocarbons could be achieved through a successive zirconocene-mediated allylic C-H bond activations followed by a selective C-C bond cleavage. Determination of the reaction mechanism by density functional theory (DFT) calculations shows that the high stereocontrol observed in this process results from a large number of energetically accessible equilibria feeding a preferred reactive channel that leads to the major product. A distinctive consequence of this pattern is that stereoselectivity is enhanced upon heating