Diastereoselective Hydrogen??Transfer Reactions: An Experimental and DFT Study

…, M Prévost, SI Gorelsky, P Mochirian…

Index: Brazeau, Jean-Francois; Mochirian, Philippe; Prevost, Michel; Guindon, Yvan Journal of Organic Chemistry, 2009 , vol. 74, # 1 p. 64 - 74

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Citation Number: 6

Abstract

Abstract Radical reductions of halogenated precursors bearing a heterocycle exo (α) to the carbon-centered radical proceed with enhanced anti-selectivity, a phenomenon that we termed “exocyclic effect”. New experimental data and DFT calculations at the BHandHLYP/TZVP level demonstrate that the origin of the exocyclic effect is linked to the strain energy required for a radical intermediate to reach its reactive conformation at the ...