83333-73-7Relevant articles and documents
Ligand-controlled cobalt-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes
Huang, Jiaxin,Li, Jie,Yang, Wen,Zhang, Kezhuo,Zhao, Pei,Zhao, Wanxiang
supporting information, p. 302 - 305 (2022/01/03)
The Co-catalyzed remote hydroboration and alkene isomerization of allylic siloxanes were realized by a ligand-controlled strategy. The remote hydroboration with dcype provided borylethers, while xantphos favored the formation of silyl enol ethers.
Silver oxide(I) promoted Conia-ene/radical cyclization for a straightforward access to furan derivatives
Ardisson, Janick,Lannou, Marie-Isabelle,Mohamed, Selkti,Sorin, Geoffroy,Yu, Bao
supporting information, p. 1374 - 1377 (2022/02/11)
A novel access to fused furan cores using silver oxide(I) has been developed. Mechanistic investigations indicate the involvement of a Conia-ene reaction/radical cyclization for an expedient path to complex furan derivatives. The reaction is broad in scop
Highly diastereoselective and enantiospecific allylation of ketones and imines using borinic esters: Contiguous quaternary stereogenic centers
Chen, Jack L.-Y.,Aggarwal, Varinder K.
supporting information, p. 10992 - 10996 (2015/03/30)
3,3-Disubstituted allylic boronic esters are not sufficiently reactive to react with ketones and imines. However they can be converted into the corresponding borinic esters by the sequential addition of nBuLi and TFAA. These reactive intermediates possess
Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium
Dobmeier, Michael,Herrmann, Josef M.,Lenoir, Dieter,Koenig, Burkhard
supporting information; experimental part, p. 330 - 336 (2012/05/20)
The synthetic protocol for the reduction of alcohols to hydrocarbons by using hydriodic acid, first described by Kiliani more than 140 years ago, was improved to be more applicable to organic synthesis. Instead of a strongly acidic, aqueous solution, a biphasic toluene-water reaction medium was used, which allowed the conversion of primary, secondary and tertiary benzylic alcohols, in good yields and short reaction times, into the corresponding hydrocarbons. Red phosphorous was used as the stoichiometric reducing agent. Keto, ester, amide or ether groups are tolerated, and catalytic amounts of hydriodic acid (0.2 equiv) in the presence of 0.6 equiv phosphorous are sufficient to achieve conversion.
One-pot synthesis of optically active allyl esters via lipase-vanadium combo catalysis
Akai, Shuji,Hanada, Ryosuke,Fujiwara, Noboru,Kita, Yasuyuki,Egi, Masahiro
, p. 4900 - 4903 (2011/01/12)
The combination of vanadium-oxo compounds (3 or 4) with a lipase produced the regio- and enantioconvergent transformation of racemic allyl alcohols (1 or 2) into optically active allyl esters. In this system, the vanadium compounds catalyzed the continuous racemization of the alcohols along with the transposition of the hydroxyl group, while the lipase effected the chemo- and enantioselective esterification to achieve the dynamic kinetic resolution.
Synthesis of vinyl 1,2-diketones
Habel, Lothar W.,De Keersmaecker, Sigrid,Wahlen, Joos,Jacobs, Pierre A.,De Vos, Dirk E.
, p. 4057 - 4059 (2007/10/03)
A new route is outlined for preparation of vinyl 1,2-diketones via a three-step sequence. First, allylic alcohols are photooxidized by 1O2 to hydroperoxides, which are reduced to vinyl 1,2-diols. These vinyl 1,2-diols are oxidized to vinyl 1,2-diketones with oxoammonium salts, which are prepared in situ from organic nitroxyl radicals. The new route is short, avoids the use of protecting groups, and is generally applicable to obtain aliphatic or aromatic vinyl 1,2-diketones.
A New, Simple, and Selective Palladium-Catalyzed Cleavage of Triethylsilyl Ethers
Rotulo-Sims, Delphine,Prunet, Joelle
, p. 4701 - 4704 (2007/10/03)
(Equation Presented) A simple procedure for the cleavage of triethylsilyl (TES) ethers in the presence of 10 wt % Pd/C in methanol or 95% ethanol is reported. This method allows selective removal of alkyl TES ethers in the presence of aromatic TES ethers or tert-butyldimethylsilyl (TBS) protecting groups.
Stereochemistry and mechanism of vinyl-migrating [1,2]-Wittig rearrangement of α-lithioalkyl vinyl ethers
Tomooka, Katsuhiko,Inoue, Tadashi,Nakai, Takeshi
, p. 418 - 419 (2007/10/03)
Enantiomerically defined α-stannylalkyl or α-methylbenzyl vinyl ethers, when treated with butyllithium, are shown to undergo the 1,2-vinyl migration to afford the allylic alcohols in almost racemic form in low or high yield, respectively, thereby proposin
Preparation and opioid activity of analogues of the analgesic dipeptide 2,6-dimethyl-L-tyrosyl-N-(3-phenylpropyl)-D-alaninamide
Chandrakumar,Yonan,Stapelfeld,Savage,Rorbacher,Contreras,Hammond
, p. 223 - 233 (2007/10/02)
A number of analogues of the recently disclosed analgesic dipeptide 2,6- dimethyl-L-tyrosyl-D-alanine-phenylpropylamide (SC-39566, 2) were prepared. These analogues contained oxymethylene, aminomethylene, ketomethylene, bismethylene, and trans double bond (including vinyl fluoride) isosteric replacements for the amide bond between the D-alanine and phenylpropylamine units in 2. These compounds were tested in opioid binding assays and in the mouse writhing assay for analgesic activity. Though not as potent as 2, the oxymethylene, and trans double bond isosteres showed analgesic activity. The aminomethylene analogues also showed binding activity in subnanomolar concentrations at the μ receptor. The amide bond between 2,6-dimethyl-L- tyrosine and D-alanine units seems to be critical for opioid activity.