Organic Letters
Organic Letters
5 years ago

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

From Hydrindane to Decalin: A Mild Transformation through a Dyotropic Ring Expansion
Yagamare Fall, Carlos Silva López, Olalla Nieto Faza, Hugo Santalla, Generosa Gómez
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01621

DOI: 10.1021/acs.orglett.7b01621

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