14090-60-9Relevant academic research and scientific papers
α-carbonyl radical cyclization approach toward spiro[4.4]nonene: Total synthesis of dimethyl gloiosiphone A
Sha, Chin-Kang,Ho, Wen-Yueh
, p. 2709 - 2710 (1998)
The total synthesis of dimethyl gloiosiphone A 2 was achieved via an α-carbonyl radical spirocyclization.
Interconversions of C5H10O+. ions with the oxygen on the first, second and third carbons: Approximately 60 communicating isomers
McAdoo,Hudson
, p. 492 - 496 (1995)
The structures of the C4H7O+ and C3H6O+. dissociation products from selected C5H10O+. isomers with the oxygen on the first, second and third carbons were determined. The first product is CH3C(OH)CH=CH2+ and the second is CH3C(OH+)CH2. and CH3.CHCHOH+ in various proportions. These results demonstrate that ions with the oxygen on the first and third carbons isomerize partially to isomers with the oxygen on the second carbon. This and C5H10O+. isomers expected to be accessible to each other suggest that there are traversable pathways between about 60 C5H10O+. isomers, demonstrating how extensive interconversions of aliphatic radical cations can be.
Intramolecular cycloadditions of vinylketenes to olefins. Part II. The synthesis of a linear annelated triquinane derivative.
Mesmaeker, Alain De,Veenstra, Siem J.,Ernst, Beat
, p. 459 - 462 (1988)
Regioselective formation of vinylketene 3, followed by its stereoselective intramolecular cycloaddition with an olefin, yielded the linear annelated cis-anti-cis triquinane precursor 1.
Converting cycloalkanones into N-heterocycles: Formal synthesis of (-)-gephyrotoxin 287C
Pichette, Simon,Winter, Dana K.,Lessard, Jean,Spino, Claude
, p. 12532 - 12544 (2013)
The photochemical rearrangement of N-activated lactams enables their ring contraction concomitant with the migration of a carbon onto a nitrogen atom. When coupled with the Beckmann rearrangement, this photochemical ring contraction converts cycloalkanones into N-heterocycles in a few steps and in a stereospecific manner. To showcase the method, we performed an efficient formal synthesis of (-)-gephyrotoxin 287C.
Tertiary Enamide-Triggered SEAr: Domino Allylation and Enamine-Type Addition
Beltran, Frédéric,Miesch, Laurence
supporting information, p. 1569 - 1573 (2019/03/12)
Two unprecedented domino reactions are described, starting from ketospiro-enesulfonamides. By treatment with ZrCl4 and allylsilane, an intramolecular electrophilic aromatic substitution and subsequent allylation is observed. By treatment with TiCl4 and allylsilane, a double enamine-type reaction takes place, thus creating simultaneously four contiguous stereogenic centers diastereoselectively.
Mechanistic Study and Development of Catalytic Reactions of Sm(II)
Maity, Sandeepan,Flowers, Robert A.
supporting information, p. 3207 - 3216 (2019/02/19)
Samarium diiodide (SmI2) is one of the most widely used single-electron reductants available to organic chemists because it is effective in reducing and coupling a wide range of functional groups. Despite the broad utility and application of SmI2 in synthesis, the reagent is used in stoichiometric amounts and has a high molecular weight, resulting in a large amount of material being used for reactions requiring one or more equivalents of electrons. Although few approaches to develop catalytic reactions have been designed, they are not widely used or require specialized conditions. As a consequence, general solutions to develop catalytic reactions of Sm(II) remain elusive. Herein, we report mechanistic studies on catalytic reactions of Sm(II) employing a terminal magnesium reductant and trimethylsilyl chloride in concert with a noncoordinating proton donor source. Reactions using this approach permitted reductions with as little as 1 mol % Sm. Mechanistic studies provide strong evidence that during the reaction, SmI2 transforms into SmCl2, therefore broadening the scope of accessible reactions. Furthermore, this mechanistic approach enabled catalysis employing HMPA as a ligand, facilitating the development of catalytic Sm(II) 5-exo-trig ketyl olefin cyclization reactions. The initial work described herein will enable further development of both useful and user-friendly catalytic reactions, a long-standing, but elusive goal in Sm(II) chemistry.
Enantioselective Conia-Ene-Type Cyclizations of Alkynyl Ketones through Cooperative Action of B(C6F5)3, N-Alkylamine and a Zn-Based Catalyst
Cao, Min,Yesilcimen, Ahmet,Wasa, Masayuki
supporting information, p. 4199 - 4203 (2019/04/13)
An efficient and highly enantioselective Conia-ene-type process has been developed. Reactions are catalyzed by a combination of B(C6F5)3, an N-alkylamine and a BOX-ZnI2 complex. Specifically, through cooperative
Method development for the determination of 1,1-dimethylhydrazine by the high-performance liquid chromatography–mass spectrometry technique
Susinskis, Igors,Mekss, Peteris,Hmelnickis, Juris
, p. 352 - 359 (2018/07/31)
Unsymmetrical dimethyl hydrazine is highly toxic, carcinogenic compound, widely used for organic synthesis and drug development. Therefore, due to its high reactivity, direct analysis is problematic. Current study proposes to use derivatization reaction t
One-pot sequential 1,4- and 1,2-reductions of α,β-unsaturated δ-lactones to the corresponding δ-lactols with CuCl and NaBH 4 in methanol
Matsumoto, Yasunobu,Yonaga, Masahiro
supporting information, p. 1764 - 1768 (2014/08/05)
An efficient, one-pot method for the highly chemoselective synthesis of δ-lactols from α,β-unsaturated δ-lactones using CuCl and NaBH4 in methanol was developed. Georg Thieme Verlag Stuttgart. New York.
Intramolecular reductive ketone-alkynoate coupling reaction promoted by (η2-propene)titanium
Schaefer, Christian,Miesch, Michel,Miesch, Laurence
supporting information; scheme or table, p. 3253 - 3257 (2012/06/01)
Intramolecular reductive coupling of cycloalkanones tethered to alkynoates in the presence of (η2-propene)titanium was successfully performed to provide hydroxy-esters in a diastereoselective manner. Subsequent lactonization afforded angularly
