92735-08-5Relevant articles and documents
InCl3/Me3SiBr-catalyzed direct coupling between silyl ethers and enol acetates
Onishi, Yoshiharu,Nishimoto, Yoshihiro,Yasuda, Makoto,Baba, Akio
supporting information; experimental part, p. 2762 - 2765 (2011/08/02)
A combined Lewis acid catalyst of InCl3 and Me3SiBr promoted the direct use of enol acetates in the coupling with low-reactive silyl ethers, in which functional groups including ketones and aldehydes survived. Sterically hindered silyl ethers such as ROSiEt3, ROSiPh3, ROSit-BuMe2, and ROSii-Pr3 were also applicable.
Efficient o-trimethylsilylation of alcohols and phenols with trimethylsilyl azide catalyzed by tetrabutylammonium bromide under neat conditions
Amantini,Fringuelli,Pizzo,Vaccaro
, p. 6734 - 6737 (2007/10/03)
A very efficient procedure for the trimethylsilylation of a wide variety of alcohols, including primary, allylic, benzylic, secondary, hindered secondary, tertiary, and phenols is reported. The reactions were carried out under neat conditions with trimethylsilyl azide (TMSN3) and, when necessary, in the presence of a catalytic amount (20 mol %) of tetrabutylammonium bromide (TBABr) at 30 or 70 °C. Under catalytic conditions, the yields of the corresponding trimethylsilyl ethers were greater than 91%. This procedure also allows the selective protection of primary and secondary alcohols in the presence of tertiary ones.
Iodohydrin Synthesis from Simple and Functionalised Olefins on Treatment with Periodic Acid and Sodium Bisulfite
Ohta, Hirofumi,Sakata, Yasuyuki,Takeuchi, Toshiyuki,Ishii, Yasutaka
, p. 733 - 736 (2007/10/02)
Periodic acid (H5IO6) in combination with sodium bisulfite was found to be a prominent reagent to convert simple and functionalised olefins into the corresponding iodohydrins in fair to good yields under mild conditions.Allylic alcohols gave iodohydrins w
SYNTHESIS OF BOTH ENANTIOMERS OF ERYTHRO-6-ACETOXY-5-HEXADECANOLIDE, THE MAJOR COMPONENT OF A MOSQUITO OVIPOSITION ATTRACTANT PHEROMONE
Sato, Toshio,Watanabe, Makoto,Honda, Naoki,Fujisawa, Tamotsu
, p. 1175 - 1176 (2007/10/02)
Stereoselective synthesis of both (5S,6R)-(+)- and (5R,6S)-(-)-6-acetoxy-5-hexadecanolides, the major component of a mosquito oviposition attractant pheromone, was achieved from (S)-2-cyclohexen-1-ol.
159. On the Stereochemistry of Allylmetal-Aldehyde Condensations
Denmark, Scott E.,Weber, Eric J.
, p. 1655 - 1660 (2007/10/02)
The stereochemical course of the intramolecular allylsilane-aldehyde condensation of 1a has been investigated.A modest preference for the product arising from a synclinal orientation of double bonds was observed with Lewis-acid catalysts.Cyclization induced by fluoride ion resulted in stereochemical reversal.
Ring Opening of Oxiranes by Trimethylsilyl Trifluoromethanesulfonate
Murata, Sizuaki,Suzuki, Masaaki,Noyori, Ryoji
, p. 247 - 254 (2007/10/02)
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-trimethylsiloxybicyclooctane.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-butyldimethylsiloxy-17β-methyl-17α--18-nor-5α-androst-13(14)-ene. α-Pinene oxide gives trans-carveol trimethylsilyl ether.
TRIMETHYLSILYL TRIFLATE IN ORGANIC SYNTHESIS
Noyori, R.,Murata, S.,Suzuki, M.
, p. 3899 - 3910 (2007/10/02)
Trimethylsilyl triflate is a powerful silylating agent for organic compounds and acts as a catalyst which accelerates a variety of nucleophilic reactions in aprotic media.The reactions proceed via one-center, electrophilic coordination of the silyl group to hetero functional groups and exhibit unique selectivities.
Method for the preparation of a triorganosilylated 2,3-unsaturated alcohol
-
, (2008/06/13)
The invention provides a novel method for the preparation of a triorganosiloxy derivative of a 2,3-unsaturated alcohol which is a useful intermediate compound for the synthetic preparation of various kinds of organic compounds. The method comprises reacti
STEPWISE CONVERSION OF OXIRANES TO ALLYLIC ALCOHOLS BY IODOTRIMETHYLSILANE AND DBU
Sakurai, Hideki,Sasaki, Koshi,Hosomi, Akira
, p. 2329 - 2332 (2007/10/02)
Iodotrimethylsilane, prepared from hexamethyldisilane and iodine, reacts smoothly with oxiranes to give (2-iodoalkoxy)trimethylsilanes which can be converted to allylic alcohols with DBU in good yields.The whole conversion can be carried out in one-pot operation.
