Studies towards enantioselective metal-catalysed nucleophilic allylations using allenes
Publication Date
March 15, 2020
Creator
Abstract
The enantioselective intramolecular nickel-catalysed nucleophilic 1,2-allylation of ketones with (hetero)arylboronic acids or potassium vinyltrifluoroborate and progress towards the enantioselective intramolecular 1,4-allylation of enones with dialkylzinc nucleophiles are described. The first project is initiated by carbonickelation of allenes which gives the nucleophilic allylnickel species that cyclise by 1,2-allylation onto a tethered ketone to produce a range of chiral tertiaryalcohol containing aza- and carbocycles in excellent diastereo- and enantioselectivities. The second project is initiated by the oxidative cyclisation of Pd(0) with an allene tethered to an enone. The resulting palladacycle formed undergoes transmetalation with a dialkylzinc nucleophile, and subsequent reductive elimination affords 6,5-fused bicycles in high diastereoselectivity.
Item Type
ethesis
Thesis Type
PhD
Supervisors
Subjects (LC)
Associated Schools / Departments
School of Chemistry
eprints ID
59565
UoN Repository URI
Except where otherwise noted, this item's license is described as
File(s)![Thumbnail Image]()
Name
Riccardo Di Sanza Thesis Corrected.pdf
Type
Full-text
Description
Examined
Size
6.37 MB
Format
Adobe PDF
Checksum (MD5)
73ebd79471766de2b4c7d45135714fe9