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Title: Stereo controlled Synthesis Using Morpholinone Chiral Templates
Author: Dix, Matthew
ISNI:       0000 0001 3425 375X
Awarding Body: The University of Reading
Current Institution: University of Reading
Date of Award: 2006
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This thesis details the attempted synthesis of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives from the (5R)-5-phenylmorpholin-2-one chiral template, and the synthesis of cycloadducts generated via 1,3-dipolar cycloadditions of the (5S)-5-phenylmorpholin-2-one cyclic template with various heterodipolarophiles. (' The account commences with a' brief introduction into the chemistry of tetrahydroisoquinolines, and their occurrences in nature. Also given are examples of some recent advances in the total synthesis of various tetrahydroisoquinolines, via the PictetSpengler synthesis, and the Bischler-Napieralski reaction. The account continues with a brief introduction to the origins of the project, and the main aims of this part of the thesis. In the second chapter, an introduction into the chemistry of chiral azomethine ylids is given, including some examples of applications of this chemistry, to the synthesis of some naturally occurring target compounds. The account closes with the aims of this part of the thesis. The third chapter details the attempted synthesis of 1,2,3,4-tetrahydroisoquinoline-3carboxylic acid derivatives via Pictet-Spengler reactions of amines derived from the cyclic (5R)-5-phenylmorpholin-2-one chiral template. Also given is an account of the attempted synthesis of similar tetrahydroisoquinolines, via the Bischler-Napieralski reaction of various ~.. amides, also derived from the cyclic template. The chapter closes with a summary of the results, and suggestions for future work. The fourth chapter begins by detailing the synthesis of some chiral azomethine ylids, derived from the (5S)-5-phenylmorpholin-2-one template, and their subsequent 1,3-dipolar cycloadditions. It is shown that cycloadducts accessed via this method require two equivalents of aldehyde, one to generate the ylid, and a further equivalent to act as the dipolarophile. Since this requirement would not be appropriate where the aldehyde is the ; limiting material, the account continues with the studies that were initiated to find a derivate of (5S)-5-phenylmorpholin-2-one that was capable of generating the ylid without the need for an aldehyde, and their subsequent trapping protocols with suitable dipolarophiles. The chapter ends with a summary of the results, and suggestions for future studies. /
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available