DBU-Promoted Dynamic Kinetic Resolution in Rh-Catalyzed Asymmetric Transfer Hydrogenation of 5‑Alkyl Cyclic Sulfamidate Imines: Stereoselective Synthesis of Functionalized 1,2-Amino Alcohols

Dynamic kinetic resolution (DKR)-driven
asymmetric transfer hydrogenation
of 5-alkyl cyclic sulfamidate imine produces the corresponding sulfamidate
with excellent levels of diastereo- and enantioselectivity by employing
a HCO2H/DBU mixture as the hydrogen source in the presence
of the Noyori-type chiral Rh-catalyst at room temperature for 1 h.
In this process, DKR was induced by DBU-promoted rapid racemization
of the substrate. Stereoselective transformations of the resulting
cyclic sulfamidates to functionalized enantiomerically enriched 1,2-amino
alcohol and chiral amine substances are also described.