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Chirality Transfer from the Oxidative Dearomatization of Axially Chiral Binols with Oxone under Mild Conditions

2020; American Chemical Society; Volume: 22; Issue: 15 Linguagem: Inglês

10.1021/acs.orglett.0c02194

1523-7060

Antonio Urbano, Sara Vallejo, María Jesús Cabrera‐Afonso, Elena Yonte,

Asymmetric Synthesis and Catalysis

Easily accessible axially chiral substituted binols (95 to >99% ee) undergo an oxidative dearomatization process with the system Oxone/NaHCO3/acetone, under mild conditions, to afford pentacyclic hemiacetalic cis-diols (94 to >99% ee), bearing two new stereogenic centers, through an efficient axial-to-central chirality transfer.