Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/15648
Title: Recoverable chiral auxiliary for the stereo-controlled preparation of phoshorothioate oligonucleotides and design of proline derivatives for aldol reactions
Authors: LIU HAI
Keywords: recoverable chiral auxiliary, phoshorothioate olignucleotides, proline derivatives, organocatalysts, aldol reaction, picket-spengler condensation.
Issue Date: 9-Mar-2007
Source: LIU HAI (2007-03-09). Recoverable chiral auxiliary for the stereo-controlled preparation of phoshorothioate oligonucleotides and design of proline derivatives for aldol reactions. ScholarBank@NUS Repository.
Abstract: In the first part of this thesis, chiral auxiliary 24 was synthesized. The novel chiral auxiliary 24 containing an amide functionality was easily derived from tryptophan. The key stereogenic center in 24 was generated by the Pictet-Spengler condensation. The chiral auxiliary 24 was applied in the stereoselective synthesis of phosphorothioates through a sequence of reactions with phosphorus trichloride and properly protected thymidine. However, the desired cyclic phosphoramidite could not be formed. Relevant model systems were then synthesized and studied, and we proposed that the neighboring group participation may be responsible for such failure of cyclic phosphoramidite formation. In the second part, several proline derived organocatalysts containing thiourea moieties were synthesized. These catalysts may prove to be useful in many asymmetric organic transformations.
URI: http://scholarbank.nus.edu.sg/handle/10635/15648
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