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Aids in asymmetric synthesis

Donovan, Anthony Richard (1998) Aids in asymmetric synthesis. PhD thesis, Murdoch University.

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The aims of this investigation were twofold. 1) Development of a practical diagnostic NMR reagent. 2) Novel C2 symmetric ligands for asymmetric synthesis.

1) Naturally occurring (+)-camphor was chosen as the basis for this programme ie the synthesis of homochiral isocyanates for use as NMR diagnostic reagents.

Isocyanates 11, 39, 46 and 56 were synthesised via a wide range of synthetic techniques and these novel compounds and their precursors treated to comprehensive In addition all were subjected to reaction with suitable However, although these structural characterisation. alcohols to determine the enantio-diagnostic value, compounds reacted in the desired manner, none have exhibited the desired diagnostic ability.

2) (R,R)- and (S,S)-l,3-Diphenyl-l,3-propanediol 86 are useful C2 chiral auxiliaries.

A number of oxidative and catalytic techniques were employed in an attempt to synthesise these compounds. Kinetic resolution via Sharpless epoxidation finally served as the key step in our successful synthesis. The cyclohexyl analogues of these enantiomerically pure diols, as well as a number of novel and interesting phosphorus and nitrogen derivatives, were also prepared. These compounds present themselves as a promising range of ligands for future exploitation in catalytic asymmetric synthesis.

*compound diagrams of (1) & (2) can be seen on page x

Item Type: Thesis (PhD)
Murdoch Affiliation(s): Division of Science
Notes: Note to the author: If you would like to make your thesis openly available on Murdoch University Library's Research Repository, please contact: Thank you.
Supervisor(s): Roos, Gregory
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