Diastereoselective remote C-H activation by hydroboration.
Hydroboration of tetrasubstituted or trisubstituted alkenes with BH(3) and subsequent thermolysis allows remote diastereoselective C-H activation of neighboring aryl rings. Tetrasubstituted and trisubstituted 1,1-diphenylethylene derivatives undergo a highly stereoselective 1,2-rearrangement followed by remote C-H activation to lead, after oxidative workup, to a diol in which the relative stereochemistry of two stereocenters has been controlled. The mechanism of this remote activation has been studied and extended to related molecules that undergo this stereoselective C-H activation, namely alkenylbiphenyl systems or alkenes with only one phenyl ring, such as alkenylbenzenes, or bicyclic systems. We have shown that this reaction allows diastereoselective synthesis of molecules with up to three contiguous chiral centers.
Varela
Jesús A
JA
Departamento de Química Orgánica y Unidad Asociada al CSIC, Facultad de Química, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
Peña
Diego
D
Goldfuss
Bernd
B
Denisenko
Dmitri
D
Kulhanek
Jiri
J
Polborn
Kurt
K
Knochel
Paul
P