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Goodrich, Oliver H. (2023) Investigations into N-Sulfinyl Imino Esters as Versatile Reagents for the Synthesis of N-Sulfinyl Compounds and Unnatural α-Amino Acid Derivatives. PhD thesis, University of Nottingham.

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Abstract

N-Sulfinylimino esters are a highly versatile class of compounds, they are already widely used within the pharmaceutical industry for the preparation of chiral α-amines. This work further explores their use as versatile reagents for the synthesis of unnatural α-amino acid derivatives and novel cyclic sulfinamides.

We investigated and expanded on the stereoselective synthesis of N-sulfinyl amines using an additive free radical 1,3-migration of N-sulfinylimino esters. This allowed the preparation of several tertiary alkyl α-amino esters via the hydrolysis of an N-sulfinyl amine intermediate.

Investigations into this migration led to the development of a novel method for the gram-scale production of tert-leucine ethyl ester in one-step from an N-sulfinyl imino ester using mild conditions and an inexpensive Lewis acid catalyst.

Building on previous literature we prepared 4 novel bicyclic sulfinamides in moderate yields using a Lewis acid mediated [3+2] cycloaddition between cycloalkenes and tert-butyl N-sulfinyl imino esters.

Item Type:	Thesis (University of Nottingham only) (PhD)
Supervisors:	Stockman, Robert
Keywords:	Sulfinimines, Unnatural Amino Acids, Sulfinamides
Subjects:	Q Science > QD Chemistry > QD241 Organic chemistry
Faculties/Schools:	UK Campuses > Faculty of Science > School of Chemistry
Item ID:	76823
Depositing User:	Goodrich, Oliver
Date Deposited:	10 Jan 2024 16:00
Last Modified:	10 Jan 2024 16:00
URI:	https://eprints.nottingham.ac.uk/id/eprint/76823

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