From Hydrindane to Decalin: A Mild Transformation through a Dyotropic Ring Expansion

An
unexpected ring expansion converting hydrindane cores into decalins
has been observed. The process occurs under very mild conditions and
with exquisite transfer of chiral information. The ring expansion
provides access to decorated decalins with complete stereocontrol.
The reaction mechanism is studied in order to gain insight into the
underlying causes for the low thermal requirements in this reaction
and the nature of the chirality transfer process. Interestingly, both
result from an unprecedented dyotropic reaction involving a mesylate
group.