A new highly stereoselective rearrangement of acyclic tertiary organoboranes: An example of highly stereoselective remote CH activation

…, F Lhermitte, RM Gschwind, P Knochel

Index: Laaziri, Hamid; Bromm, Lars O.; Lhermitte, Frederic; Gschwind, Ruth M.; Knochel, Paul Journal of the American Chemical Society, 1999 , vol. 121, # 29 p. 6940 - 6941

Full Text: HTML

Citation Number: 32

Abstract

The activation of allylic CH bonds is an important reaction, which has attracted much attention. Most results have been obtained with cyclic systems. 1 Recently, we have shown that an efficient allylic CH activation can be formally realized by the hydroboration of tetrasubstituted cycloalkenes with BH3 in THF followed by a smooth thermal rearrangement. 2, 3 We are pleased to report that this rearrangement can be performed with acyclic ...