3043-65-0Relevant academic research and scientific papers
The influence of α-coordinating groups of aldehydes on E/Z-selectivity and the use of quaternary ammonium counter ions for enhanced E-selectivity in the Julia–Kocienski reaction
Rehman, Mintu,Surendran, Sravya,Siddavatam, Nagendra,Rajendar, Goreti
supporting information, p. 329 - 333 (2022/01/20)
Modified reaction conditions for improved E-selectivity of olefins in the Julia–Kocienski reaction of aldehydes having α-coordinating substituents are demonstrated. The chelating groups in aldehydes are expected to stabilize the syn-transition state with metal ions, whereas the weakly coordinating quaternary ammonium ions are devoid of all possible chelating interactions to enhance E-selectivity. A systematic investigation is presented to study the size of the neighbouring protecting groups of aldehydes and their chelation effect on E/Z-selectivity in the Julia–Kocienski reaction.
One-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols
Ando, Kaori,Hattori, Junichiro
, (2019/08/12)
A method for one-pot preparation of Julia-Kocienski sulfides and sulfones from alcohols and thiols is reported. A variety of primary alcohols were converted to the corresponding mesylates by methansulfonyl chloride and triethylamine in THF. After the reaction is complete, thiol (1 or 10) and either NaH or t-BuOK were added. The Julia-Kocienski sulfides 3, 9 and 11 were prepared by one-pot two steps procedure from alcohols in 76–96% yields (16 examples). Furthermore, after the sulfide formation, the reaction mixture was neutralized by p-toluenesulfonic acid and treated with H2O2 and ammonium molybdate in EtOH to give the Julia-Kocienski sulfones 4 in good yields except for trans-2-hexen-1-ol.
THIOREDOXIN AND THIOREDOXIN REDUCTASE INHIBITORS
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Page/Page column 58; 13/22; 14/22, (2008/06/13)
The present invention relates to sulfone derivatives and to their use as modulators of the thioredoxin/thioredoxin reductase redox system, including for the treatment and/or prevention of pathophysiological conditions mediated by thioredoxin/thioredoxin reductase, such as cancer, HIV/ AIDS, Alzheimer's disease, rheumatoid arthritis, and skin disorders. Also provided are pharmaceutical compositions comprising the inventive sulfones.
(R)-Goniothalamin: Total syntheses and cytotoxic activity against cancer cell lines
De Fatima, Angelo,Kohn, Luciana Konecny,Antonio, Marcia Aparecida,De Carvalho, Joao Ernesto,Pilli, Ronaldo Aloise
, p. 2927 - 2933 (2007/10/03)
The total syntheses of (R)-goniothalamin (1), a styryl lactone isolated from several Goniothalamus species, via catalytic asymmetric allylation of α-benzyloxyacetaldehyde (2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of trans-cinnamaldehyde (12), followed by ring-closing metathesis are reported. The antiproliferative activities of (R)-1 and its Z-isomer 10 as well as of the synthetic dihydropyranone intermediates 7 and 8 against eight different cancer cell lines are also described.
Tetrazoles. XXXI. Phase-Transfer Reactions of 1-Substituted Tetrazole-5-thiones and Their Derivatives
Gol'tsberg,Koldobskii
, p. 1194 - 1201 (2007/10/03)
Alkylation of 1-substituted tetrazole-5-thiones under conditions of phase-transfer catalysis in the two-phase system liquid-liquid proceeds regioselectively at the sulfur atom, regardless of the alkylating agent and phase-transfer catalyst. Phase-transfer oxidation of the 5-alkylthiotetrazoles thus obtained by potassium permanganate is a convenient method for preparation of 5-alkylsulfonyltetrazoles which can be used to synthesize functionally substituted tetrazoles.
