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Acid-catalysed hydroaminations

Henderson, Laura 2010. Acid-catalysed hydroaminations. PhD Thesis, Cardiff University.

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Abstract

The Knight group has for some time been utilising the acid-catalysed hydroamination to synthesise pyrrolidines 140. This method was also utilised to produce poly-cyclic systems, of either a spiro- 220 or a fused-nature 12, through cascade reactions using a sulfonamide as a terminator. This was examined further to establish some scope and limitation. In particular, we have shown that the reaction is not limited to the formation of tertiary carbenium ions but could be implemented for cyclisations via secondary carbenium ions 155. The hydroamination was also shown to be most successful at forming highly hindered, bridged compounds 194, which would be difficult to synthesise through other means. The hydroamination reaction was then investigated in terms of its potential as a variant of the classical Pictet-Spengler reaction towards dihydroisoindoles 363 and tetrahydroisoquinolines 361. This was briefly explored in terms of the type of remote functional groups that would be compatible with this method. The formation of the isoindoles and isoquinolines was successful and further investigations of compatible functional groups need to be performed. The synthesis of the trisubstituted piperidine 447 was attempted using the acid-catalysed hydroamination method, believing that this would be a simple extension of the pyrrolidine synthesis. Unfortunately, this was not successful; instead the corresponding pyrrolidine 449 was isolated. This led us to further investigate the sensitivity of sterically crowded piperidines towards acid. Successful synthesis of trisubstituted piperidine 501 was achieved by changing the JV-protecting group.

Item Type: Thesis (PhD)
Status: Unpublished
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Funders: EPSRC, Eli Lilley
Date of First Compliant Deposit: 30 March 2016
Last Modified: 19 Mar 2016 23:29
URI: http://orca-mwe.cf.ac.uk/id/eprint/54172

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