Synthesis of cyclic sulfoximines and their application in the expedient synthesis of cyclic sulfinamides and 3-pyrrolines

Ward, Jon-Paul (2019) Synthesis of cyclic sulfoximines and their application in the expedient synthesis of cyclic sulfinamides and 3-pyrrolines. PhD thesis, University of Nottingham.

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The synthesis of sulfoximines has been studied since the late 1940s but their application in academia and industry has only started to be exploited over the last 20 years.

In 2013, a novel [2,3]-sigmatropic rearrangement of 2-vinylaziridines to cyclic sulfoximines (R2 = mesityl or tert-butyl) was discovered by the Stockman group. The first project investigates the de-tert-butylation of tert-butyl sulfoximines (R2 = tert-butyl) to afford the unprecedented chiral cyclic sulfinamides. This has enabled a two-step telescoped protocol to be developed, whereby chiral cyclic sulfinamides can be prepared from readily available tert-butyl sulfinimines.

The second project revisits a previous finding within the Stockman group, which was the ring contraction of mesityl cyclic sulfoximines (R2 = mesityl). The scope of the existing [2,3]-sigmatropic rearrangement to afford mesityl cyclic sulfoximines is expanded. Subsequently, the scope of the novel ring contraction of mesityl cyclic sulfoximines to 3-pyrrolines in one step is greatly expanded.

Finally, the third project concerns the further functionalisation of the cyclic sulfoximine and cyclic sulfinamide products, which were produced during the first and second projects. This small study is only an introduction into the potential of these novel three-dimensional structures.

Item Type: Thesis (University of Nottingham only) (PhD)
Supervisors: Stockman, Robert
Keywords: Synthesis of cyclic sulfoximines, cyclic sulfinamides and 3-pyrrolines going via a [3,3]-sigmatropic rearrangement of 2-vinylaziridines, Organosulphur compounds
Subjects: Q Science > QD Chemistry > QD241 Organic chemistry
Faculties/Schools: UK Campuses > Faculty of Science > School of Chemistry
Item ID: 56191
Depositing User: Ward, Jon-Paul
Date Deposited: 04 Sep 2019 10:43
Last Modified: 07 May 2020 08:30

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