34553-37-2Relevant academic research and scientific papers
SUBSTITUTED STRAIGHT CHAIN SPIRO DERIVATIVES
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Page/Page column 91, (2021/06/26)
Provided herein are pharmaceutical agents useful for therapy and/or prophylaxis in a mammal, pharmaceutical composition comprising such compounds, and their use as menin/MLL protein/protein interaction inhibitors, useful for treating diseases such as cancer, including but not limited to leukemia, myelodysplastic syndrome (MDS), and myeloproliferative neoplasms (MPN); and diabetes.
A convenient route to chiral γ-lactones via asymmetric hydrogenation of γ-ketoesters using the RuCl3-BINAP-HCl catalytic system
Starodubtseva, Eugenia V.,Turova, Olga V.,Vinogradov, Maxim G.,Gorshkova, Lilia S.,Ferapontov, Vladimir A.,Struchkova, Marina I.
experimental part, p. 11713 - 11717 (2009/04/11)
A convenient one-step synthesis of chiral γ-lactones has been performed. The method is based on enantioselective hydrogenation of γ-ketoesters using the RuCl3-BINAP-HCl catalytic system. Chiral γ-lactones (91-99% ee) have been isolated in 57-88% yield.
QUINALDYL ETHERS AS LATENT CARBONYL FUNCTIONS
Rukachaisirikul, Vatcharin,Koert, Ulrich,Hoffmann, Reinhard W.
, p. 4533 - 4544 (2007/10/02)
Ketones can be generated from secondary alcohols by converting the latter into quinaldine ethers followed by irradiation (>320 nm).The quinaldine ethers can therefore be utilized as latent carbonyl groups.The quinaldine group is chemically inert during transformations at other parts of the molecule involving hydroboration, Grignard reagents, LiAlH4, as well as bromine or ozone. Key Words: Ketone formation, photochemical; Protecting group
APPLICATIONS OF THE THERMAL ENE REACTION OF ALDEHYDE t-BUTYL- AND PHENYL- HYDRAZONES
Baldwin, Jack E.,Adlington, Robert M.,Jain, Ashok U.,Kolhe, Jayant N.,Perry, Matthew W. D.
, p. 4247 - 4252 (2007/10/02)
The Thermal Ene reaction of aldehyde t-butyl- and phenyl- hydrazones with enophiles gave C-trapped azo-adducts which can be diverted into synthetically useful γ-keto-esters, γ-keto-nitriles, γ-alkyl-2-pyrrolidones, and γ-amino-esters.
Michael Additions of Hydrazones for Carbon-Carbon Bond Formation
Baldwin, Jack E.,Adlington, Robert M.,Bottaro, Jeffrey C.,Jain, Ashok U.,Kolhe, Jayant N.,et al.
, p. 1095 - 1096 (2007/10/02)
The lithium salts of t-butyl- and trityl-hydrazones react with methyl crotonate to form C-trapped azo-esters and similar products were observed from a thermal ene-reaction of aldehyde t-butylhydrazones with methyl acrylate or acrylonitrile, and aldehyde phenylhydrazones with methyl acrylate; these products can be diverted into synthetically useful γ-keto-esters, γ-keto-nitriles, saturated esters, γ-alkyl-2-pyrrrolidones, and γ-amino-esters.
Ring Opening Reactions of Methyl 2-Siloxycyclopropanecarboxylates to Oxoalkanoic Acid Derivatives
Kunkel, Elisabeth,Reichelt, Ingrid,Reissig, Hans-Ulrich
, p. 802 - 819 (2007/10/02)
A great variety of methyl 2-(trialkylsiloxy)cyclopropanecarboxylates C1 - C31 are cleaved under very mild conditions and with excellent yields providing 4-oxoalkanoic esters D1 - D31 which are important synthetic building blocks.Even sensible esters with formyl, vinyl ketone, or trimethylsiloxy functions can be prepared.Corresponding to the regioselective synthesis of C isomeric pairs of D can deliberately be constructed.In the presence of an electrophile alkylating ring opening delivers 4-oxoalkanoates substituted in position 2, however, the degree of alkylation does not exceed 60percent.Several other cleavage variations allow syntheses of other 4-oxoalkanoic acid derivatives in effective one-pot procedures.
Electroorganic Chemistry. Part 73. Electroreductive Cross-coupling of 3-Substituted Alkanoic Acid Esters with Aldehydes or Acid Anhydrides
Shono, Tatsuya,Matsumura, Yoshihiro,Kashimura, Shigenori
, p. 1922 - 1935 (2007/10/02)
Elecroreductive cross-coupling reaction of 3-phenylthioalkanoic acids esters (4a) or quaternary ammonium salts of 3-aminoalkanoic acid esters (4b) with aldehydes gave the corresponding γ-lactones in one step.The cross-coupling reaction of (4b) with acid anhydrides leading to the formation of the corresponding γ-keto esters is also described.
CATALYTIC REDUCTION OF 3-(4,4-DIMETHYL-5-KETO-3-ISOXAZOLE)PROPIONIC ACID AND ITS DERIVATES
Feuer, Henry,Scholl, Philip C.
, p. 29 - 35 (2007/10/02)
Catalytic hydrogenation of 3-(4,4-dimethyl-5-keto-3-isoxazole)propionic acid (1) in glacial acetic acid in the presence of 5percent palladium on charcoal gives 4-amino-5-methylhexanoic acid (2).Reductions of the corresponding esters, methyl 3-(4,4-dimethyl-5-keto-3-isoxazole)propionate (3) and amide, 3-(4,4-dimethyl-5-keto-3-isoxazole)propionamide (4) afford, however, γ-isopropylbutyrolactam (5).Reductions of 1 and 3 in aqueous acetic acid give 4-keto-5-methylhexanoic acid (6) and methyl 4-keto-5-methylhexanoate (7), respectively.On the other hand amide 4 is converted to2-hydroxy-5-isopropylidene-Δ1-pyrroline (8).Compound 8 is also obtained if 4 is reduced in acetic acid containing a small amount of hydrogen chloride.
Fluoride-Mediated Reactions of Enol Silyl Ethers. Regiospecific Monoalkylation of Ketones
Kuwajima, Isao,Nakamura, Eiichi,Shimizu, Makoto
, p. 1025 - 1030 (2007/10/02)
Treatment of enol silyl ethers with alkyl halides in the presence of benzyltrimethylammonium fluoride and molecular sieves at room temperature gives the corresponding monoalkylated products with high regiospecificity.In most cases no polyalkylated products formed in the reaction.The alkylation reaction is highly chemospecific: esters, epoxides, and even ketones survive the reaction conditions.The reactions of various cyclohexanone derivatives proceed with the preferential axial attack of the electrophile.
