Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/134474
Title: IRIDIUM/CHIRAL PHOSPHORIC ACID CATALYZED ENANTIOSELECTIVE AMINATION OF ALCOHOLS AND ORGANOCATALYTIC ENANTIOSELECTIVE OXIDATION OF 1,2-DIOLS
Authors: RONG ZIQIANG
Keywords: enantioselectivity, borrowing hydrogen, amination, alcohols, cooperative catalysis, organocatalysis
Issue Date: 5-Aug-2016
Source: RONG ZIQIANG (2016-08-05). IRIDIUM/CHIRAL PHOSPHORIC ACID CATALYZED ENANTIOSELECTIVE AMINATION OF ALCOHOLS AND ORGANOCATALYTIC ENANTIOSELECTIVE OXIDATION OF 1,2-DIOLS. ScholarBank@NUS Repository.
Abstract: Chiral alcohols and amines have proven to be important structural motifs presented in numerous biologically active natural products, synthetic compounds and drugs, and they have also been widely found in chiral auxiliaries, ligands and catalysts. In this thesis, we have developed a highly efficient enantioselective oxidation of meso-diols catalyzed by quinine-derived Lewis basic catalyst and enantioselective amination of α-branched alcohols by the use of borrowing hydrogen methodology through a unique “double” dynamic kinetic process. Under the cooperative catalysis by an iridium complex and a chiral phosphoric acid, α-branched alcohols that exist as a mixture of four isomers undergo racemization by two orthogonal mechanisms and are converted to diastereo- and enantiopure amines bearing adjacent stereocenters. In addition, the dynamic kinetic asymmetric synthesis of biologically active tetralin- and indane-derived chiral amines using microwave-assisted borrowing hydrogen has also been realized.
URI: http://scholarbank.nus.edu.sg/handle/10635/134474
Appears in Collections:Ph.D Theses (Open)

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