Ontology highlight
ABSTRACT:
SUBMITTER: Munoz A
PROVIDER: S-EPMC3546829 | biostudies-literature | 2012 Dec
REPOSITORIES: biostudies-literature
Munoz Alberto A Murelli Ryan P RP
Tetrahedron letters 20121012 50
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), γ-methyl-γ-hydroxybutenolide reacts with aromatic aldehydes to generate a new class of stereochemically rich spirocyclic ketal-lactones in good yields and with excellent stereoselectivities. We believe that this process takes place through the in situ generation of protoanemonin followed by a Prins reaction. Herein, we describe this discovery, along with substrate scope and preliminary mechanistic studies. ...[more]