Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/61843
Title: Functionalization of aldehydes via n-heterocyclic carbene and base organic catalysts
Authors: Yang, Ruojie
Keywords: DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
Issue Date: 2014
Source: Yang, R. (2014). Functionalization of aldehydes via n-heterocyclic carbene and base organic catalysts. Doctoral thesis, Nanyang Technological University, Singapore.
Abstract: In this thesis, direct and efficient functionalization of aldehydes with organocatalysts towards synthetic attractive molecules is presented. Chapter II describes the direct α-functionalization of simple aldehydes under oxidative NHC catalysis and the direct generation of ester enolates by using simple nonfunctionalized aldehydes as substrates. The same transformation with only catalytic amount of quinone-derived oxidant can be realized by using much cheaper terminal oxidants MnO2, providing an economic solution for large scale industrial synthesis. Chapter III presents the [3+2] annulations of isatin and β-branched unsaturated aldehyde catalyzed by N-heterocyclic carbene. Synthetic attractive spirocyclic oxindole products are synthesized in generally good yield and diastereoand enantioselectivity. Followed in chapter IV, the first base catalyzed in-situ generation of enesulfonamide is discussed. This enamide derivative underwent facile formal [4+2] addition reactions with α,β-unsaturated imines, producing highly substituted tetrahydropyridines as single diasteromer, which possess huge potential in the synthesis of pharmaceutical and biological compounds.
In this thesis, direct and efficient functionalization of aldehydes with organocatalysts towards synthetic attractive molecules is presented. Chapter II describes the direct α-functionalization of simple aldehydes under oxidative NHC catalysis and the direct generation of ester enolates by using simple nonfunctionalized aldehydes as substrates. The same transformation with only catalytic amount of quinone-derived oxidant can be realized by using much cheaper terminal oxidants MnO2, providing an economic solution for large scale industrial synthesis. Chapter III presents the [3+2] annulations of isatin and β-branched unsaturated aldehyde catalyzed by N-heterocyclic carbene. Synthetic attractive spirocyclic oxindole products are synthesized in generally good yield and diastereoand enantioselectivity. Followed in chapter IV, the first base catalyzed in-situ generation of enesulfonamide is discussed. This enamide derivative underwent facile formal [4+2] addition reactions with α,β-unsaturated imines, producing highly substituted tetrahydropyridines as single diasteromer, which possess huge potential in the synthesis of pharmaceutical and biological compounds.
URI: http://hdl.handle.net/10356/61843
metadata.item.grantfulltext: embargo_21141103
metadata.item.fulltext: With Fulltext
Appears in Collections:SPMS Theses

Files in This Item:
File Description SizeFormat 
YRJ-Thesis2014Oct.pdf
  Until 2114-11-03
YRJThesis5.49 MBAdobe PDFThumbnail
View/Open    Request a copy

Page view(s)

282
checked on Dec 26, 2019

Download(s)

109
checked on Dec 26, 2019

Google ScholarTM

Check

Items in DR-NTU are protected by copyright, with all rights reserved, unless otherwise indicated.