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

Hyeong Rae Kim; Raghavendra Achary; Hyeon-Kyu Lee

doi:10.1021/acs.joc.8b01892

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

J Org Chem. 2018 Oct 5;83(19):11987-11999. doi: 10.1021/acs.joc.8b01892. Epub 2018 Sep 17.

Authors

Hyeong Rae Kim^{1

2}, Raghavendra Achary¹, Hyeon-Kyu Lee^{1

2}

Affiliations

¹ Korea Chemical Bank , Korea Research Institute of Chemical Technology , PO Box 107, Yuseong, Daejeon 305-600 , Korea.
² Department of Medicinal Chemistry and Pharmacology , University of Science and Technology , 113 Gwahango , Yuseong, Daejeon 305-333 , Korea.

PMID: 30199258
DOI: 10.1021/acs.joc.8b01892

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't