2816-63-9Relevant articles and documents
Facile synthesis of c/s-2-alkyl-3-trialkylsilyloxycycloalkanones via the non-aldol aldol rearrangement of 2,3-epoxycycloalkanols
Jung, Michael E.,Allen, Damian A.
supporting information; experimental part, p. 2039 - 2041 (2009/04/18)
Silyl triflate-promoted rearrangement of c/s-2,3-epoxycycloalkanols A, prepared by epoxidation of the cyclic allylic alcohol and then sllylatlon, afforded good yields (~70-75%) of the c/s-2-alkyl-3-silyloxycycloalkanones B, presumably via the intermediates C and D, even with quite large α-substituents, e.g., terf-butyl. Finally, it has been shown that the stereochemistry of the epoxy alcohol is crucial as one would expect from the mechanism.