Absolute configuration determination and convenient asymmetric synthesis of cis-3-(9-Anthryl)cyclohexanol with proline as a catalyst.
cis-(3R)-(9-anthryl) derivative of cyclohexanol was conveniently obtained in enantiomerically pure form from 2-cyclohexenone using asymmetric Michael addition of anthrone catalyzed by l-proline in a key step. The absolute configuration of the addition product was unequivocally determined by means of electronic circular dichroism measurements combined with calculation of the circular dichroism spectrum by using a density functional theory method.
Department of Chemistry, Adam Mickiewicz University, Poznan, Poland.
Jędrzej
J
Wysocki
Marcin
M
Kwit
Jacek
J
Gawronski