Asymmetric dehydration of β-hydroxy esters via kinetic resolution

Dehydration reactions in polyfunctional natural products

“…The use of a Reformatsky reagent (111) in enantioselective synthesis of β-hydroxy ester derivatives, such as R- (110), through activity of a prolinol-derived chiral ligand (112), was the stepping-stone for the discovery of a kinetic resolution that furnishes the enantiopure β-hydroxy esters by dehydration. 138 Scheme 23: Example of a kinetic resolution to furnish enantiopure R- (110), by selective dehydration of the L-enantiomer of the β-hydroxy ester (110) to the corresponding alkene (113). The conditions use a Reformatsky-type reagent (111) in combination with catalytic quantities of a chiral ligand (112).…”

Palladacycle-Catalyzed Highly Efficient Kinetic Resolution of 1-Hydroxy-2-aryl-1,2-dihydronaphthalenes via Dehydration Reaction

“…Ring-opening reactions of epoxides ,, and aziridines, epoxidation and dihydroxylation of alkenes, − acylation, oxidative transfer hydrogenation, Baeyer−Villiger reaction, hydrogenation of alkenes and imines, , ring-closing metathesis, Pd-catalyzed allylic alkylation, , cyclopropanation using diazoesters, alcoholysis of anhydrides, 1,4-conjugated addition, and cycloaddition reaction are among the most general types of reactions used in kinetic resolution. However, few reports achieved kinetic resolution via dehydration reaction of alcohols though it is a very common type of reaction in organic synthesis . Furthermore, there are no reports of using palladacycles as catalysts in kinetic resolution.…”