%0 Journal Article %A Lynch, Denis %A Deasy, Rebecca E. %A Clarke, Leslie-Ann %A Slattery, Catherine N. %A B. Rao Khandavilli, U. %A Lawrence, Simon E. %A Maguire, Anita R. %A Magnus, Nicholas A. %A Moynihan, Humphrey A. %D 2016 %T Exploring the Scope of Asymmetric Synthesis of β‑Hydroxy-γ-lactams via Noyori-type Reductions %U https://acs.figshare.com/articles/journal_contribution/Exploring_the_Scope_of_Asymmetric_Synthesis_of_Hydroxy-_-lactams_via_Noyori-type_Reductions/3848637 %R 10.1021/acs.orglett.6b02416.s003 %2 https://acs.figshare.com/ndownloader/files/6022857 %K β- keto -γ-lactams %K diastereoselective hydrogenation %K Full conversion %K bioactive compounds %K Asymmetric Synthesis %K β- hydroxy -γ-lactams %K ketone substituent %K Noyori-type Reductions Enantio %X Enantio- and diastereoselective hydrogenation of β-keto-γ-lactams with a ruthenium–BINAP catalyst, involving dynamic kinetic resolution, has been employed to provide a general, asymmetric approach to β-hydroxy-γ-lactams, a structural motif common to several bioactive compounds. Full conversion to the desired β-hydroxy-γ-lactams was achieved with high diastereoselectivity (up to >98% de) by addition of catalytic HCl and LiCl, while β-branching of the ketone substituent demonstrated a pronounced effect on the modest to excellent enantioselectivity (up to 97% ee) obtained. %I ACS Publications