Asymmetric Hydrogenation of Racemic α‑Aryl-β-ethoxycarbonyl
Cyclopentanones via Dynamic Kinetic Resolution and Its Application
to the Synthesis of (+)-Burmaniol A
posted on 2021-10-28, 18:47authored byYing Xiong, Han Lin, Chang-Liang Zhu, Yong-Hong Chen, Rong Ye, Guan-Wen Hu, Jian-Hua Xie, Qi-Lin Zhou
An efficient asymmetric hydrogenation
of racemic α-aryl-β-ethoxycarbonyl
cyclopentanones via dynamic kinetic resolution is reported. Via catalysis
by a chiral iridium Ir-SpiroPAP catalyst, a range of racemic α-aryl-β-ethoxycarbonyl
cyclopentanones were hydrogenated to the corresponding ester-functionalized
chiral 2-arylcyclopentanols with three contiguous stereocenters in
high yields with excellent enantio- and diastereoselectivities. This
method was successfully applied in the enantioselective synthesis
of cyclopentane-based γ-amino ester/alcohol derivatives and
phenylpropanoid (+)-burmaniol A.