14733-20-1Relevant academic research and scientific papers
One-Pot Bi(OTf)catalyzed oxidative deprotection of tert -butyldimethyl silyl ethers with TEMPO and co-oxidants
Barnych, Bogdan,Vatèle, Jean-Michel
experimental part, p. 2048 - 2052 (2011/10/19)
A sequential one-pot synthesis for the oxidation of primary and secondary tert-butyldimethylsilyl (TBDMS) ethers, using catalytic amounts of metal triflates and TEMPO in combination with PhIO or PhI(OAc)in THF or acetonitrile, is described. Acid-sensitive protecting groups such as methylidene, isopropylidene, acetals, and Boc are unaffected under the reaction conditions. Another feature of this procedure is its high selectivity for TBDMS ethers over tert-butyldiphenylsilyl ethers and of aliphatic TBDMS groups over phenolic TBDMS groups. Georg Thieme Verlag Stuttgart - New York.
Application of the excited state meta effect in photolabile protecting group design
Wang, Pengfei,Hu, Ayou,Wang, Yun
, p. 2831 - 2833 (2008/02/07)
A novel photolabile protecting group for carbonyl compounds has been developed, based on the excited state meta effect.
Palladium(II)-catalyzed oxidation of alcohols to aldehydes and ketones by molecular oxygen
Nishimura, Takahiro,Onoue, Tomoaki,Ohe, Kouichi,Uemura, Sakae
, p. 6750 - 6755 (2007/10/03)
A novel combination of Pd(OAc)2/pyridine/MS3A catalyzes the aerobic oxidation in toluene of a variety of primary and secondary alcohols into the corresponding aldehydes and ketones in high yields. Various substituents and protecting groups are compatible with this oxidation. The ca. 2:3 ratio of O2 uptake to product yield is observed, whereas in the absence of MS3A, the ratio is ca. 1:1, suggesting the in situ formation of H2O2 and its decomposition by MS3A into water and oxygen. A catalytic cycle including the formation of a Pd(II)-alcoholate followed by β-elimination of a Pd(II)H species and a carbonyl compound and then the formation of a Pd(II)OOH species is proposed.
ZINC CHLORIDE-MEDIATED CONJUGATE REDUCTION WITH SILICON HYDRIDES AND PALLADIUM(0) CATALYST
Keinan, Ehud,Greenspoon, Noam
, p. 1353 - 1356 (2007/10/02)
The chemistry of diphenylsilane/Pd(0), a system previously known to reduce only allylic heterosubstituents, has been radically altered by addition of catalytic amounts of zinc chloride, enabling efficient conjugate reduction of α,β-unsaturated ketones and aldehydes.
CONVERSION OF THE ALLYLIC AND HOMOALLYLIC STEROIDAL ALCOHOLS TO THE CORRESPONDING SATURATED KETONES BY MEANS OF THE ACTIVATED Ra/Ni
Forsek, Joze
, p. 1071 - 1074 (2007/10/02)
Conversion of the allylic and homoallilyc alcohols (1) and (2) to the corresponding saturated ketones (3) and (4), by means of the activated Ra/Ni, in the presence of cyclohexanone, was achieved stereospecifically and high yields.
Silanes in Organic Synthesis. 9. Enesilylation as a Method for 1,2-Carbonyl Migration within Ketones and for Conversion to 1,2-Transposed Allylic Alcohols
Fristad, William E.,Bailey, Thomas R.,Paquette, Leo A.
, p. 3028 - 3037 (2007/10/02)
Vinylsilanes are shown to be valuable synthetic intermediates in useful transformations of ketones.The epoxidation of vinylsilanes followed by lithium aluminium hydride reduction and oxidation with chromic acid and sulfuric acid in a two-phase (ether/water) system often gives high yields of 1,2-transposed ketones.With singlet oxygen and sequential sodium borohydride reduction, 2-trimethylsilyl alcohols are produced in which the α position of the parent ketone has been regiospecifically oxygenated.Fluoride ion promoted desilylation completes the conversion to the migrated allylic alcohol.
OXIDATION OF ALCOHOLS WITH OXOPEROXOBIS-(N-PHENYLBENZOHYDROXAMATO)MOLYBDENUM(VI)
Tomioka, Hiroki,Takai, Kazuhiko,Oshima, Koichiro,Nozaki, Hitosi,Toriumi, Koshiro
, p. 4843 - 4846 (2007/10/02)
The title complex oxidizes primary and secondary alcohols to the corresponding carbonyl compounds.Stereoselective epoxidation of allylic alcohols is also described.
