Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 19, Pages 11987-11999Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01892
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Funding
- National Research Foundation of Korea [2017M3A9A5051181]
- Korea Research Institute of Chemical Technology [SI1707, SI1807]
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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.
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