Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/62121
Full metadata record
DC FieldValueLanguage
dc.contributor.authorBai, Yaguangen
dc.date.accessioned2015-01-21T04:56:24Zen
dc.date.available2015-01-21T04:56:24Zen
dc.date.copyright2014en
dc.date.issued2014en
dc.identifier.citationBai, Y. (2014). Palladium catalyzed reactions on glycal scaffolds : syntheses of glycal derivatives and c-glycosides. Doctoral thesis, Nanyang Technological University, Singapore.en
dc.identifier.urihttps://hdl.handle.net/10356/62121en
dc.description.abstractGlycals are a group of carbohydrate derivatives which were first synthesized more than a century ago. The reactive carbon-carbon double bond between C1 and C2 has stimulated a huge number of efforts to develop new carbon-carbon bond formation methods to transform glycals into other carbohydrate analogues and various useful synthetic building blocks. Palladium catalyzed carbon–carbon bond formation reaction has become a fast growing area of chemistry due to its versatility and chemo selectivity. Palladium catalyzed reactions such as Heck–Mizoroki reaction, Suzuki reaction and Tsuji–Trost reaction have been intensively studied in the past decades. This thesis focuses on applying palladium chemistry to glycals to develop new methodologies on glycal functionalizations. In the first chapter, a new Pd(OAc)2 catalyzed direct alkene-alkene coupling of glycals and other alkenes such as acrylates and styrenes is described. The concept of this methodology is to apply the palladium catalyzed C–H activation on glycal functionalizations. The coupling reaction selectively takes place on C2 of the glycals to form sugar containing dienes. In the second chapter, a Heck type C-glycosylation of glycals and enol triflates is demonstrated. In this reaction, the Nobel winning Heck reaction is applied on glycals to give exclusively C1 regioselectivity and α stereoselectivity. The substrate scope includes glycals from different sugar origins and enol triflates of different sizes. Another Heck type α selective C-glycosylation methodology of glycals and aryl hydrazines towards aryl-C-glycosides is reported in the third chapter. The mechanism of α selectivity is also studied in this chapter. In the last chapter, a dual catalyzed reaction by integrating the renowned palladium catalyzed Tsuji–Trost reaction and NHC catalysis is introduced. The two catalysts exert their effects simultaneously and parallelly to afford the nucleophilic addition product. The concept is first tried on simple allylic system and then on glycals with ethoxycarbonyloxyl protecting group on C3. In both cases, the aldehyde origins of the nucleophilic Breslow intermediate are o-azaarylcarboxaldehydes.en
dc.format.extent197 p.en
dc.language.isoenen
dc.subjectDRNTU::Science::Chemistry::Organic chemistry::Carbohydratesen
dc.titlePalladium catalyzed reactions on glycal scaffolds : syntheses of glycal derivatives and C-glycosidesen
dc.typeThesisen
dc.contributor.supervisorLiu Chuan Faen
dc.contributor.supervisorLiu Xueweien
dc.contributor.schoolSchool of Physical and Mathematical Sciencesen
dc.description.degreeDOCTOR OF PHILOSOPHY (SPMS)en
dc.identifier.doi10.32657/10356/62121en
item.fulltextWith Fulltext-
item.grantfulltextopen-
Appears in Collections:SPMS Theses
Files in This Item:
File Description SizeFormat 
Thesis SPMS G1001347K.pdf5.48 MBAdobe PDFThumbnail
View/Open

Page view(s) 20

676
Updated on Mar 27, 2024

Download(s) 20

277
Updated on Mar 27, 2024

Google ScholarTM

Check

Altmetric


Plumx

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