58558-53-5Relevant academic research and scientific papers
Dehydrative/decarboxylative coupling of carboxylic acids with allylic alcohols
Masuda, Yusuke,Ito, Misato,Murakami, Masahiro
supporting information, p. 1030 - 1033 (2021/05/19)
Herein reported is a dehydrative/decarboxylative coupling reaction of carboxylic acids with allylic alcohols, which is cocatalyzed by photoredox and palladium catalysts. α-Hetero- or aryl-substituted carboxylic acids and allylic alcohols, which are both readily available, directly participate in CC bond formation without any functional group transformation.
Direct Hydrofluorination of Methallyl Alkenes Using a Methanesulfonic Acid/Triethylamine Trihydrofluoride Combination
Bertrand, Xavier,Paquin, Jean-Fran?ois
supporting information, p. 9759 - 9762 (2019/11/28)
The use of a methanesulfonic acid/triethylamine trihydrofluoride combination for the direct hydrofluorination of methallyl-containing substrates is reported. Under those metal-free conditions that use readily available, cheap, and easy to handle reagents,
Tandem ring-closing metathesis/transfer hydrogenation: Practical chemoselective hydrogenation of alkenes
Connolly, Timothy,Wang, Zhongyu,Walker, Michael A.,McDonald, Ivar M.,Peese, Kevin M.
supporting information, p. 4444 - 4447 (2015/01/09)
An operationally simple chemoselective transfer hydrogenation of alkenes using ruthenium metathesis catalysts is presented. Of great practicality, the transfer hydrogenation reagents can be added directly to a metathesis reaction and effect hydrogenation of the product alkene in a single pot at ambient temperature without the need to seal the vessel to prevent hydrogen gas escape. The reduction is applicable to a range of alkenes and can be performed in the presence of aryl halides and benzyl groups, a notable weakness of Pd-catalyzed hydrogenations. Scope and mechanistic considerations are presented.
SPIRO-OXINDOLE MDM2 ANTAGONISTS
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Page/Page column 150-151, (2011/05/16)
Provided herein are compounds, compositions, and methods in the field of medicinal chemistry. The compounds and compositions provided herein relate to spiro-oxindoles which function as antagonists of the interaction between p53 and MDM2, and their use as
Metal-catalyzed rearrangement of homoallylic ethers to silylmethyl allylic silanes in the presence of a di-tert-butylsilylene source
Cleary, Pamela A.,Woerpel
, p. 5531 - 5533 (2007/10/03)
(Chemical Equation Presented) In examining the scope of the di-rert-butylsilylene transfer to gem-disubstituted alkenes to form silacyclopropanes, we discovered an unprecedented reaction of homoallylic ethers. When silylene transfer was performed at room
Syntheses of novel 4-tert-alkyl ether proline-based 16- and 17-membered macrocyclic compounds
Chen, Kevin X.,Njoroge, F. George,Vibulbhan, Bancha,Buevich, Alexei,Chan, Tze-Ming,Girijavallabhan, Viyyoor
, p. 2730 - 2733 (2007/10/03)
Starting from N-Cbz-4-hydroxyproline methyl ester 1, a boron trifluoride-diethyl etherate-catalyzed reaction provided 4-tert-alkyl ether proline 4. Two deprotections and amide bond formations furnished the phenol alcohol 2. The macrocyclization of 2 was accomplished through a Mitsunobu reaction using triphenylphosphine and 1,1′-(azodicarbonyl)dipiperidine (ADDP), to afford novel 16- and 17-membered proline-based macrocyclic compounds of type 3.
Synthesis and characterization of new malolactonate polymers and copolymers for biomedical applications
Bizzarri, Ranieri,Chiellini, Federica,Solaro, Roberto,Chiellini, Emo,Cammas-Marion, Sandrine,Guerin, Philippe
, p. 1215 - 1223 (2007/10/03)
A new class of malolactonate polymers and copolymers were synthesized, starting from the corresponding lactones, and then characterized. Different lateral groups were selected for these polyesters to achieve a wide range of materials characteristics and possible biological recognition. The monomers were prepared according to two established procedures, which gave rather good overall yields. The polymers were obtained by the anionic ring-opening polymerization of the corresponding four-member ring monomers in the presence of a quaternary ammonium salt as the initiator. Final macromolecular and thermal characteristics were in agreement with the designed monomer structures. Molecular weights in the range 4-20 kDa were obtained, as a result of chain transfer reactions. The prepared polyesters displayed stability up to 200°C, and, when tested in preliminary cell culture experiments, provided indications for future applications in the biomedical field.
New olefination of acetals with TMSCH2Cu(PBu3)·LiI under the influence of BF3·OEt2
Suzuki, Takeshi,Oriyama, Takeshi
, p. 859 - 861 (2007/10/03)
Peterson-type olefination of acetals can be conveniently performed by reaction with TMSCH2Cu(PBu3)LiI, which is prepared in-situ from TMSCH2Li, CuI and PBu3, under the influence of BF3·OEt2 via Lewis acid-promoted β- elimination of β-alkoxysilanes.
Pigments of Fungi. LIX - Synthesis of (1S,3S)- and (1R,3R)-austrocortilutein and (1S,3S)-austrocortirubin from citramalic acid
Gill, Melvyn,Harte, Michael F.,Ten, Abilio
, p. 245 - 256 (2007/10/03)
The naturally occurring tetrahydroanthraquinone (1S,3S)-austrocortilutein (1) is synthesized for the first time in enantiomerically pure form by Diels-Alder cycloaddition between the functionalized butadiene derivative (8) and the chiral 1,3-dihydroxy-1,2,3,4-tetrahydro-5,8-naphthoquinone (9), the latter being derived from (R)-citramalic acid (3). The natural products (1S,3S)-austrocortirubin (2) and (1R,3R)-austrocortilutein (5) were also prepared for the first time by using the same strategy. CSIRO 2000.
Preparation of chiral building blocks for a highly convergent vitamin E synthesis. Systematic investigations on the enantioselectivity of the sharpless bishydroxylation
Tietze, Lutz F.,Goerlitzer, Jochen
, p. 873 - 878 (2007/10/03)
The enantioselective bishydroxylation of protected 2-methylprop-2-enol 15 and 3-methylbut-3-en-1-ol 16 to give the corresponding diols 18 and 19, respectively, which can be transformed into building blocks for the synthesis of natural vitamin E, is described. It is shown that the enantioselectivity of the bishydroxylation reaction clearly depends on the type of protecting group and its distance from the alkene moiety, with 96% ee for 16a and 16f as the best and 8% ee for 15d as the lowest result.
