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Acid-mediated coupling of ?-hydroxybutenolides and aldehydes: Synthesis of a new class of spirocyclic ketal-lactones.


ABSTRACT: In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), ?-methyl-?-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.

SUBMITTER: Munoz A 

PROVIDER: S-EPMC3546829 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: Synthesis of a new class of spirocyclic ketal-lactones.

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]

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