S. Murata, Masaaki Suzuki, R. Noyori
1982
Citations
0
Influential Citations
24
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Trimethylsilyl trifluoromethanesulfonate promotes ring opening reactions of oxirane derivatives. The reaction course is highly affected by the structures and substitution pattern of the substrates. Tetra-, tri-, and 2,2-disubstituted oxiranes and simple cycloalkene oxides are converted to the corresponding allylic alcohol trimethylsilyl ethers. The overall transformation is interpreted in terms of trans addition of the silyl trifluoromethanesulfonate to the oxirane ring followed by base-promoted anti elimination of a trifluoromethanesulfonic acid element. 2,3-Dialkyl- or monoalkyloxiranes isomerize to the corresponding ketones and aldehydes, respectively. (Z)-Cyclooctene oxide undergoes the transannular reaction to give endo-cis-2-trimethylsiloxybicyclo[3.3.0]octane. The reaction of 6-methyl-5-hepten-2-one oxide produces 2,2,6-trimethyl-3-trimethylsiloxy-3,4-dihydro-2H-pyran. 1,2-Methyl migration takes place in the reaction of (E)-3α-t-butyldimethylsiloxy-5α-pregnene 17α,20-oxide to afford 3α-t-butyldimet...