Synthesis of Optically Active Spirocycles by a Sequence of Decarboxylative Asymmetric Allylic Alkylation and Heck Reaction
Year: 2024
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide Optically active spirocycles were prepared in a sequence of two palladium-catalyzed reactions. In the first step, racemic α-( ortho -iodophenyl)-β-oxo allyl esters were submitted to the palladium-catalyzed decarboxylative asymmetric allylic alkylation reaction, furnishing the α-allylated products with a quaternary stereocenter with good yields and enantioselectivities. Subsequently, these intermediate products were converted in a Heck reaction yielding the spirocyclic structures as a mixture of exo - and endo -cyclic regioisomers. These mixtures could be isomerized with an acidic ion-exchange resin to give the endo -products with quantitative yield and selectivity. The target structure of this study could be further submitted to Friedel–Crafts reactions with electron-rich aromatic compounds.
Source: Organic Letters
Institution: Carl von Ossietzky Universität Oldenburg
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
OpenAlex ID: W4404995581