Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/35211
Title: Pentanidium Catalyzed Enantioselective Phase-Transfer Reactions
Authors: MA TING
Keywords: Phase-transfer, Pentanidium, Conjugate addition, Enantioselective, Amination reaction
Issue Date: 2-Mar-2012
Source: MA TING (2012-03-02). Pentanidium Catalyzed Enantioselective Phase-Transfer Reactions. ScholarBank@NUS Repository.
Abstract: A new chiral entity, pentanidium, has been developed and shown to be an excellent chiral phase transfer catalyst (PTC). Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various a, ?-unsaturated acceptors, such as vinyl ketones, acrylates and chalcones, were investigated under chiral pentanidium. Excellent yield and ee values were achieved. A successful gram-scale experiment at low catalyst loading of 0.05 mol% indicates the potential of practical application for this methodology. Adducts can be easily transformed to enantiopure pyrrolidines. Besides, when phophoglycine ester was applied as donor, adduct could be transformed to a-aminophosphonic acid derivatives or phosphonic analogues of proline easily. Further developments of pantanidium were conducted: large scale synthesis, modification of pentanidium, proline derived pentanidiuim synthesis. Pentanidium has also been successfully employed in asymmetric amination of glycine derivatives. a-Amination product was transformed to Bz protected chiral aminal with excellent ee.
URI: http://scholarbank.nus.edu.sg/handle/10635/35211
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01 Chapter 1.pdf1.66 MBAdobe PDF

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05 Appendix-NMR Spectra.pdf8.27 MBAdobe PDF

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