Investigations into N-Sulfinyl Imino Esters as Versatile
Reagents for the Synthesis of N-Sulfinyl Compounds and
Unnatural α-Amino Acid Derivatives
Publication Date
December 12, 2023
Creator
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
ethesis
Thesis Type
PhD
Supervisors
Subjects (LC)
Associated Schools / Departments
School of Chemistry
eprints ID
76823
UoN Repository URI
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Thesis FINAL.pdf
Type
Full-text
Description
Examined
Size
4.3 MB
Format
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