Facile Synthesis Of Salmochelin S1, S2and Ni-Catalyzed Reductive Allylation Of Unactivated Alkyl Halides With Allylic Carbonates

This thesis describes two different projects. The first section emphasizes facilesynthesis of two kinds of linear salmochelin S1and S2which are Fe3+siderophoresin blood cells. The second section focuses on the process of Ni-catalyzed reductiveallylation of unactivated alkyl halides with allylic carbonates. This mild,easy-to-handle method allows excellent functional group tolerance, and providesallyl products in moderate to excellent yields.1) Salmochelin S1and S2were prepared through amide bond connection to anary C-glucosyl acyl chloride (Ar1COCl) and serine ester amines, followed byhydrogenolysis of the per-benzylated precursors. Each synthesis employed ahighly diastereoselective Ni-catalyzed Negishi approach to the arylC-glycoside subunit.2) A Ni-catalyzed reductive allylation approach to the cross-couplingunactivated Alkyl halides with allylic carbonates has been successfullydeveloped. The reaction works efficiently for iodo and bromide compounds,with their diverse set of substituted allylic carbonates companion. The mildreaction conditions allow for excellent functional group tolerance, andprovide the allylation coupling products in moderate to excellent yields.