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Title: Development of Enantioselective Organocatalysis by Bifunctional Indane Amine-Thiourea Catalyst
Authors: REN QIAO
Keywords: Enantioselectivity, Organocatalysis, Bifunctional, Indane Scaffold, Thiourea
Issue Date: 7-Aug-2013
Citation: REN QIAO (2013-08-07). Development of Enantioselective Organocatalysis by Bifunctional Indane Amine-Thiourea Catalyst. ScholarBank@NUS Repository.
Abstract: Urea/thiourea organocatalysis has emerged as a powerful tool to synthesize chiral pharmaceutical important natural products because of its advantages in comparison with transition metal catalysis. The aim of this dissertation was to develop some novel and easily synthesized bifunctional indane amine-thiourea catalysts to promote unique enantioselective cascade reactions, resulting in assembling some densely functionalized privileged medicinal scaffolds in both organic and biological chemistry. Firstly, the design and synthesis of a small library of bifunctional indane amine-thiourea organocatalysts was described. Then, the versatile synthetic utilities of these elegant organocatalysts were successfully demonstrated in particularly practical enantioselective cascade Michael-oxa-Michael-tautomerization reaction, Michael-enolation-cyclization reaction, as well as Mannich-intramolecular ring cyclization-tautomerization sequence. Finally, a highly efficient organocatalytic decarboxylative [1,2]-addition strategy and a direct enantioselective decarboxylation of readily accessible a,?-unsaturated carbonyls and malonic acid half thioesters were disclosed to furnish some particularly important pharmaceutical natural products.
Appears in Collections:Ph.D Theses (Open)

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