Synthesis of N-Containing Compounds: Development of Methodology and its Application in Total Synthesis
Sammanfattning: This thesis aims to develop new synthetic methods and explore the possibilities to apply it in the total synthesis of natural products.Chapter 2 deals with a mild procedure for the synthesis of a-keto amides by a-oxidation of the corresponding aketo amines mediated by pyrrolidine and TEMPO. The method can also be applied to the synthesis of a-keto thioamides and a-keto amidines.Chapter 3 deals with a straightforward synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters from the corresponding racemic a-amino-b-keto esters by using ATH/DKR protocol. In order to highlight the versatility of the methodology, it was applied in an efficient asymmetric synthesis of the polyhydroxylated pyrrolizidine alkaloid (+)-alexine.Chapter 4 describes an asymmetric formal hydroamination of enamines approach using Cu-H catalyst for the synthesis of chiral 1,2-diamines. The method provides a straightforward method for the synthesis of chiral 1,2-dialkyl amines in good yields with high level of enantioselectivities for a broad range of substrates and shouldhave significant value for the preparation of molecules bearing a 1,2-diamine motif.
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