Chiral ligands are the footstones for asymmetric synthesis constructing the enantio-enriched molecules that are widely used in material and medicinal sciences. Nature occurring compounds, such as proline analogues and cinchona alkaloids, were widely used as privileged ligands in asymmetric synthesis. Sparteine, a natural alkaloid firstly reported in 1968, was also employed in asymmetric synthesis albeit with less satisfactory results. In this perspective, transition metal-involved asymmetric transformations using sparteine or the family members as ligands are overviewed and discussed. The design and perspective on ligands with similar skeleton are also proposed.
A naturally occurring alkaloid aloperine was utilized as a core chiral skeleton for the development of new ligands. Using these chiral 1,3-diamine ligands, a Pd catalysed asymmetric hydroarylation of ketimines was reported. A range of chiral sulfonyl amides were prepared in high yields and enantioselectivties. The stereoselectivity and structure relationships of aloperine has been studied by the introduction of various subsitituents. These discoveries would provide a new future development for natural product inspired chiral ligand design and developments.
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