2816-63-9Relevant academic research and scientific papers
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.
Oxidation of Enol Silyl Ethers: Preparation of Aeginetolide, Dihydroactinidiolide, and Actinidiolide
Rubottom, George M.,Juve, Henrik D.
, p. 422 - 425 (2007/10/02)
The preparation of the C11-terpenic lactones aeginetolide (1), dihydroactinidiolide (2), and actinidiolide (3) by using 1,3,3-trimethyl-2-(trimethylsiloxy)cyclohexene (9) as a common precursor is discussed.The key steps in the synthetic route involve the sequential m-chloroperbenzoic acid (MCPBA) oxidation and acetylation of 9 and of the siloxy diene 13 derived from 9.
