Differentiation of diastereotopic bromine atoms in SN2 reactions of gem-dibromides.
A novel directed S(N)2 reaction of conformationally biased gem-dibromides and an arenesulfinate anion is described. The reaction results in the diastereoselective formation of α-bromosulfones. The selectivity originates from pre-coordination of the nucleophile to a free hydroxyl group in the γ-position.
Department of Chemistry, Philipps-University of Marburg, Hans-Meerwein-Strasse, 35043 Marburg, Germany.
Niels
N
Münster
Klaus
K
Harms
Ulrich
U
Koert