Migratory Dynamic Kinetic Resolution of Carbocyclic Allylic Alcohols

A novel migratory dynamic kinetic resolution based on the interplay between an enzyme acylation catalyst and a heterogeneous Bronsted acid as an isomerization/racemization catalyst gives rise to carbocyclic allylic esters with excellent stereoselectivity from readily available tertiary carbinols. An easy-to-use teabag setup combining resin-bound catalysts, a biphasic isooctanewater solvent system, and a highly lipophilic acyl donor efficiently suppresses side reactions and allows for the preparation of functionalized carbocyclic building blocks in high yields and optical purity

Enzymatic halocyclization of allenic alcohols and carboxylates: a biocatalytic entry to functionalized O-heterocycles

Chloroperoxidase from Caldariomyces fumago catalyzes the aerobic oxidative halocyclization of allenic alcohols and carboxylates yielding functionalized furan and pyran heterocycles as valuable synthetic scaffolds. Thanks to an oxidase-initiated redox cascade, simple halide salts – in combination with air and glucose – act as stoichiometric reagents for the in situ generation of reactive halonium species. Under the mild reaction conditions in an aqueous emulsion medium, the stereochemical integrity of diastereoand enantioenriched allenes remains uncompromised and chiral dihydrofurans can be obtained via 5-endo-trig cyclizations with perfect axis-to-centre chirality transfer.Peer reviewe

Migratory Dynamic Kinetic Resolution of Carbocyclic Allylic Alcohols

A novel migratory dynamic kinetic resolution based on the interplay between an enzyme acylation catalyst and a heterogeneous Brønsted acid as an isomerization/racemization catalyst gives rise to carbocyclic allylic esters with excellent stereoselectivity from readily available tertiary carbinols. An easy-to-use teabag setup combining resin-bound catalysts, a biphasic isooctane–water solvent system, and a highly lipophilic acyl donor efficiently suppresses side reactions and allows for the preparation of functionalized carbocyclic building blocks in high yields and optical purity