143615-77-4Relevant academic research and scientific papers
Chiral benzazaboroles as catalysts for enantioselective sulfonylation of: Cis -1,2-diols
Kuwano, Satoru,Hosaka, Yusei,Arai, Takayoshi
supporting information, p. 4475 - 4482 (2019/05/16)
A newly developed benzazaborole smoothly catalyzed the enantioselective sulfonylation of cis-1,2-diols. Using a chiral benzazaborole/NMI co-catalyst system, various sulfonate esters were prepared in high yields with good enantioselectivities.
Scope of the directed dihydroxylation: Application to cyclic homoallylic alcohols and trihaloacetamides
Donohoe, Timothy J.,Mitchell, Lee,Waring, Michael J.,Helliwell, Madeleine,Bell, Andrew,Newcombe, Nicholas J.
, p. 2173 - 2186 (2007/10/03)
The synthesis and directed dihydroxylation of a range of cyclic alkenes was investigated. Both homoallylic alcohols and homoallylic trihaloacetamides were found to be efficient directing groups, giving rise to good to excellent levels of remote asymmetric induction with OsO4-TMEDA. Interestingly, in all cases examined, trifluoroacetamides were found to be superior to trichloroacetamides as directing groups and an argument is presented which rationalises this observation.
Homoallylic alcohols and trichloroacetamides as hydrogen bond donors for directed dihydroxylation
Donohoe, Timothy J,Mitchell, Lee,Waring, Michael J.,Helliwell, Madeleine,Bell, Andrew,Newcombe, Nicholas J.
, p. 8951 - 8954 (2007/10/03)
The synthesis and directed dihydroxylation of a series of homoallylic alcohols and trichloroacetamides is described. Using the combination of OsO4 and TMEDA, moderate to high levels of stereoselectivity were obtained, depending upon the structu
One-pot synthesis from 1,4-cyclohexadiene of (±)-1,4/2,5-cyclohexanetetrol, a naturally occurring cyclitol derivative
Maras, Ahmet,Erden, Mesut,Secen, Hasan,Suetbeyaz, Yasar
, p. 435 - 437 (2007/10/03)
SeO2-catalyzed direct hydroxylation of 1,4-cyclohexadiene with two molar equivalents of 30% H2O2 afforded (±)-1,4/2,5-cyclohexanetetrol, a naturally occurring cyclitol derivative, as the sole product in a good yield (88%).
Catalytic One-Pot Osmylation of Cyclohexadienes: Stereochemical and Conformational Studies of the Resulting Polyols
Tschamber, Theophile,Backenstrass, Frederique,Fritz, Hans,Streith, Jacques
, p. 1052 - 1060 (2007/10/02)
Catalytic double osmylation is described for a series of cyclohexadienes in acetone/H2O in the presence of the co-oxidant N-methylmorpholine N-oxide (NMO).The formation of polyols occurred stereospecifically with cyclohexadienes 3, 7, and 11a, leading thereby to tetrols 5a, and 9a and to allo-inositol (14a), respectively.To the contrary, trans-cyclohexadiene-diol 15a gave a mixture of the stereoisomeric inositols 18a (epi), 19a (neo), and 20a (chiro).High-field NMR let to clearcut conformational analyses of the polyhydroxylated derivatives.
