68276-71-1Relevant academic research and scientific papers
Palladium-Catalyzed Asymmetric Hydrosulfonylation of 1,3-Dienes with Sulfonyl Hydrazides
Li, Ming-Ming,Cheng, Lei,Xiao, Li-Jun,Xie, Jian-Hua,Zhou, Qi-Lin
, p. 2948 - 2951 (2020/12/15)
A highly enantio- and regioselective hydrosulfonylation of 1,3-dienes with sulfonyl hydrazides has been realized by using a palladium catalyst containing a monodentate chiral spiro phosphoramidite ligand. The reaction provided an efficient approach to synthetically useful chiral allylic sulfones. Mechanistic studies suggest that the reaction proceeds through the formation of an allyl hydrazine intermediate and subsequent rearrangement to the chiral allylic sulfone product. The transformation of the allyl hydrazine intermediate to the product is the enantioselectivity-determining step.
Efficient synthesis and biological evaluation of demethyl geranylgeranoic acid derivatives
Wada, Akimori,Wang, Fei,Suhara, Yoshitomo,Yamano, Yumiko,Okitsu, Takashi,Nakagawa, Kimie,Okano, Toshio
experimental part, p. 5795 - 5806 (2010/09/18)
Synthetic retinoids have generated in the fields of dermatology and oncology due to their potent anti-proliferative and differentiation activities. We efficiently synthesized different demethyl geranylgeranoic acid (GGA) analogs, and evaluated their biological activities. Among the demethyl analogs synthesized, 3-demethyl derivative exhibited the highest anti-proliferative activity in HL-60 cells. In addition, a 3-demethyl derivative induced apoptosis more potently than 9Z-retinoic acid. These activities were due to the high binding affinity of 3-demethyl derivative for retinoid receptors. We found that, in a conjugated polyene system combined with a methyl substituent, the position of the methyl played an important role in the regulation of gene transcription and apoptosis-inducing activity. These results provided useful information on the structure-activity relationships of GGA derivatives that function as acyclic retinoic acid analogs. This information is likely to be useful in the development of new anti-cancer drugs.
Aluminum chloride-iron promoted coupling of sulfonyl chlorides with alkyl halides in aqueous media
Saikia, Promod,Laskar, Dhrubojyoti D.,Prajapati, Dipak,Sandhu, Jagir S.
, p. 512 - 513 (2007/10/03)
A simple and inexpensive procedure for the coupling of sulfonyl chlorides and alkyl halides with aluminum chloride-iron system at ambient temperature in high yield is achieved in aqueous media.
Bi or Cd-induced coupling of sulfonyl chlorides with allylic halides. A simple synthesis of allylic sulfones
Baruah, Mukulesh,Boruah, Anima,Prajapati, Dipak,Sandhu, Jagir S.
, p. 1083 - 1084 (2007/10/03)
The bismuth or cadmium-catalyzed coupling reaction between aryl and alkyl sulfonyl chlorides and allylic halides proceeds smoothly to provide excellent yields of allylic sulfones at ambient temperature.
Palladium-Catalyzed Asymmetric Allylic Sulfonylation
Eichelmann, Holger,Gais, Hans-Joachim
, p. 643 - 646 (2007/10/02)
The palladium-catalyzed asymmetric sulfonylation of allylic substrates rac-7a,b and rac-8a,b in the presence of the chiral phosphino-oxazoline ligand 3a gave the allylic sulfones 9a and 9b with ee-values of 59percent and 88percent, respectively, in high yield.In the presence of ligand ent-3b the enantiomeric allylic sulfones ent-9a and ent-9b were obtained with ee-values of 57percent and 93percent in high yield.
"Syn-Effect" in the Conversion of (E)-Vinylic Sulfones to the Corresponding Allylic Sulfones
Hirata, Takaki,Sasada, Yoshihiro,Ohtani, Takashi,Asada, Takahiro,Kinoshita, Hideki,et al.
, p. 75 - 96 (2007/10/02)
It was found that (E)-vinylic sulfones preferentially afford (Z)-allylic sulfones as kinetically-controlled products by treatment with a base under mild conditions, while (Z)-vinylic sulfones give (E)-allylic sulfones.Such stereochemical relationship was
SH2' Type Reactions of Arenesulfonyl Chlorides with Allylic Compounds Catalyzed by a Ruthenium(II) Complex
Kamigata, Nobumasa,Ishii, Kimiko,Ohtsuka, Takeshi,Matsuyama, Haruo
, p. 3479 - 3481 (2007/10/02)
In the presence of a catalytic amount of dichlorotris(triphenylphosphine)ruthenium(II), the reactions of arenesulfonyl chlorides with allyl phenyl sulfide and allyl phenyl selenide proceeded smoothly to give allyl phenyl sulfone in high yield as well as the corresponding diphenyl disulfide or diphenyl diselenide.An SH2'-type mechanism involving the arenesulfonyl radical is proposed.
Regio- and Stereoselective Synthesis of (E)- and (Z)-Allylsulfones from Aldehydes and Alkynes
Ozawa, Motoyasu,Iwata, Noriyoshi,Kinoshita, Hideki,Inomata, Katsuhiko
, p. 1689 - 1692 (2007/10/02)
Several (E)- and (Z)-1-p-toluenesulfonyl(=tosyl)-2-alkenes, allylsulfones, were regio- and stereoselectively prepared from aldehydes and alkynes, respectively, in good yields by application of the results of our previous investigation on "syn-effect" and
Palladium-Catalyzed Allylic Sulfinate-Sulfone Rearrangements
Hiroi, Kunio,Makino, Kunitaka
, p. 1727 - 1737 (2007/10/02)
Upon treatment with a zero-valent palladium catalyst, tetrakis(triphenylphosphine)palladium, in tetrahydrofuran under mild conditions allylic p-toluenesulfinates underwent α- or γ-rearrangements of the sulfonyl group via ionic intermediates to give allylic sulfones.The regiochemistry of the rearrangements depends on the character of the intermediary allylic cationic carbons generated and the steric hindrance involved therein.Keywords - allylic sulfinate; allylic sulfone; palladium catalyst; sulfinate-sulfone rearrangement; regiochemistry; tetrakis(triphenylphosphine)palladium.
