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New Directions In The Petasis-Borono-Mannich Reaction: Application Of Organocatalysis And Allyl- And Crotylboronates For The Enantio- And Diastereoselective Synthesis Of 1,2-Fluoroamines And 1,2-Amino Alcohols, Philip James Chevis
University of Wollongong Thesis Collection 2017+
The Petasis-borono-Mannich (PBM) reaction has been shown to be effective for the synthesis of chiral small molecules as well as polyhydroxylated alkaloids and heterocycles. However, there is very limited literature surrounding the use of allylboronates in the PBM reaction. In addition, most PBM reactions use chiral pool materials as a source of α-heteroatom aldehydes, rather than a more general method. Development of both these areas in the PBM reaction would enable a more versatile synthesis of alkaloid-like skeletons than is described in current literature. In this Thesis, organocatalysis was used to synthesise chiral α-heteroatom aldehydes according to literature procedures, which …
Synthesis And Palladium-Catalysed Reactions Of Cyclic Sulfamidate Imines And Related Analogues, Quoc Hoang Pham
Synthesis And Palladium-Catalysed Reactions Of Cyclic Sulfamidate Imines And Related Analogues, Quoc Hoang Pham
University of Wollongong Thesis Collection 2017+
Five-membered cyclic sulfamidate imines—the unsaturated analogues of the well-established synthetic precursor cyclic sulfamidates—have attracted increasing interest from synthetic chemists within the last two decades, and the recent developments involving this intriguing scaffold is summarised in Chapter 1. Featuring a highly reactive imine functionality, these stereodefined heterocycles are popular substrates in various transition metal-catalysed asymmetric reactions such as hydrogenation, transfer hydrogenation, and nucleophilic addition. On the other hand, the nucleophilic reactivity of these cyclic imines, enabled by the acidic proton(s) at the α-position to the imine functionality, have also been elegantly demonstrated in several organocatalysed cascade transformations. This manuscript describes the …