Palladium-Catalyzed Intermolecular Enantioselective Oxycarbonylation Of Alkenes

Chiral β-hydroxycarboxylic acid are featured in many natural products and bioactive molecules.Prized for their pervasiveness,it is important to develop efficient synthetic methods.In this thesis,palladium-catalyzed asymmetric acetyloxycarbonylation of internal olefins and styrenes has been developed.Ⅰ Palladium-catalyzed intermolecular enantioselective oxycarbonylation of internal alkenesFirstly,the reaction used simple internal olefins as raw materials and efficiently synthesized a series of chiral β-hydroxycarboxylic acid with excellent enantioselectivity and diastereoselectivity.Then partial unsymmetrical internal olefin substrates could also produce products with high regioselectivity.This reaction exhibited broad substrate scope and functional group tolerance.Experiments on the scale of gram have proved that this reaction has certain practical value in synthetic applications.Ⅱ Palladium-catalyzed intermolecular enantioselective oxycarbonylation of internal styrenesThe reaction used styrene as raw materials and palladium-catalyzed enantioselective oxycarbonylation was initially realized.By designing chiral ligands and using suitable oxidants,β-oxyphenylpropionic acid can be obtioned with medium yields,medium enantioselectivity and high regioselectivity.