Home

A study of a chiral 4-substituted oxazolidin-2-one in asymmetric transformations via soluble polymer-supported synthesis and fluorous synthesis

Show simple item record

dc.contributor.author Sudharshan, Manjul en_US
dc.date.accessioned 2007-05-18T19:58:17Z
dc.date.available 2007-05-18T19:58:17Z
dc.date.issued 1999-07-01T00:00:00Z en_US
dc.identifier.uri http://hdl.handle.net/1993/1777
dc.description.abstract Chiral auxiliaries remain one of the most reliable ways of generating new chiral molecules in a highly enantiomerically enriched form. We have synthesized a new chiral -substituted oxazolidin-2-one from ' L'-tyrosine via a novel method. The potential of this methodology has been established. Supporting a chiral auxiliary on a polymer provides a convenient work-up and purification procedure and makes its recovery simple. Careful choice of polymer and auxiliary is essential for its success. The first synthesis of a soluble polymer-supported oxazolidinone from the tyrosine-derived oxazolidin-2-one and the soluble poly(ethylene glycol)-monomethyl ether (MeOPEG) has been described. The behavior of the MeOPEG-supported oxazolidin-2-one in the asymmetric alkylation and the Diels-Alder reaction has been disclosed. Fluorous synthesis introduces an alternative route to traditional and polymer-supported synthesis. The synthesis of a novel, highly fluorinated silyl fluorous tag has been described. The tyrosine-derivedoxazolidin-2-one has been rendered fluorous upon attachment to the fluorous tag. Asymmetric aldol condensation of the fluorous-tagged oxazolidin-2-one has produced all four diastereoisomers and their stereochemical assignments have been confirmed. This is the first demonstration of the suitability of fluorous synthesis strategy for asymmetric synthesis of chiral oxazolidinones. en_US
dc.format.extent 10337056 bytes
dc.format.extent 184 bytes
dc.format.mimetype application/pdf
dc.format.mimetype text/plain
dc.language en en_US
dc.language.iso en_US
dc.rights info:eu-repo/semantics/openAccess
dc.title A study of a chiral 4-substituted oxazolidin-2-one in asymmetric transformations via soluble polymer-supported synthesis and fluorous synthesis en_US
dc.type info:eu-repo/semantics/masterThesis
dc.type master thesis en_US
dc.degree.discipline Chemistry en_US
dc.degree.level Master of Science (M.Sc.) en_US


Files in this item

This item appears in the following Collection(s)

Show simple item record

View Statistics