Organic Letters
Organic Letters
5 years ago

Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enones to Chiral Cycloalkanols with Three Contiguous Stereocenters

Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enones to Chiral Cycloalkanols with Three Contiguous Stereocenters
Yun-Ting Liu, Lin-Ping Li, Jian-Hua Xie, Ji-Qiang Chen, Qi-Lin Zhou, Xin-Yang Shao
A highly efficient iridium-catalyzed asymmetric hydrogenation of tetrasubstituted cyclic enones has been developed for the enantioselective synthesis of chiral cycloalkanols with three contiguous stereocenters. The C═O and C═C bonds of the enone substrates were hydrogenated sequentially in one pot with excellent enantioselectivity (92 to >99% ee) and diastereoselectivity (dr 95:5 to >99:1). The reaction provided a practical approach to all of the stereoisomers of the antiulcer drug rosaprostol.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01343

DOI: 10.1021/acs.orglett.7b01343

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