- Application of Transaminases in a Disperse System for the Bioamination of Hydrophobic Substrates
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The challenging bioamination of hydrophobic substrates has been attained through the employment of a disperse system consisting of a combination of a low polarity solvent (e. g. isooctane or methyl-tert-butylether), a non-ionic surfactant and a minimal amount of water. In these conditions, amine transaminases (ATA) were shown to efficiently carry out the reductive amination of variously substituted cyclohexanones, providing good conversions often coupled with a superior stereoselectivity if compared with the corresponding chemical reductive amination. An array of synthetically useful 4-substituted aminocyclohexanes was consequentially synthesized through biocatalysis, analyzed and stereochemically characterized. (Figure presented.).
- Berglund, Per,Fiorati, Andrea,Humble, Maria S.,Tessaro, Davide
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- Process for preparing 4-phenyl cycloheptylamine
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The invention discloses a process for preparing 4-phenyl cycloheptylamine. The process comprises the following steps: 1) in the presence of a strong base, condensing 4-phenyl cyclohexanone and hydroxylammonium chloride in an appropriate solvent at an appr
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Paragraph 0017-0018
(2018/12/13)
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- Direct Catalytic Desaturation of Lactams Enabled by Soft Enolization
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A direct catalytic method is described for the α,β-desaturation of N-protected lactams to their conjugated unsaturated counterparts under mildly acidic conditions. The reaction is consistently operated at room temperature and tolerates a wide range of functional groups, showing reactivity complementary to that of prior desaturation methods. Lactams with various ring sizes and substituents at different positions all reacted smoothly. The synthetic utility of this method is demonstrated in a concise synthesis of Rolipram. In addition, linear amides also prove to be competent substrates, and the phthaloyl-protected product serves as a convenient precursor to access various conjugated carboxylic acid derivatives. Strong bases are avoided in this desaturation approach, and the key is to merge soft enolization with a Pd-catalyzed oxidation process.
- Chen, Ming,Dong, Guangbin
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supporting information
p. 7757 - 7760
(2017/06/21)
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- Directing Group in Decarboxylative Cross-Coupling: Copper-Catalyzed Site-Selective C-N Bond Formation from Nonactivated Aliphatic Carboxylic Acids
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Copper-catalyzed directed decarboxylative amination of nonactivated aliphatic carboxylic acids is described. This intramolecular C-N bond formation reaction provides efficient access to the synthesis of pyrrolidine and piperidine derivatives as well as the modification of complex natural products. Moreover, this reaction presents excellent site-selectivity in the C-N bond formation step through the use of directing group. Our work can be considered as a big step toward controllable radical decarboxylative carbon-heteroatom cross-coupling.
- Liu, Zhao-Jing,Lu, Xi,Wang, Guan,Li, Lei,Jiang, Wei-Tao,Wang, Yu-Dong,Xiao, Bin,Fu, Yao
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supporting information
p. 9714 - 9719
(2016/08/11)
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- Synthesis of oximes with NH2OH.HCl/DOWEX(R)50WX4 system
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The oximation of a variety of carbonyl compounds was efficiently carried out with DOWEX(R)50WX4/NH2OH·HCl system. The reactions were performed in ethanol to give Z-aldoximation isomers of aldehydes and E-oximaton of acetophenone derivatives in a perfect selectively. The oximation of compounds with two carbonyl groups was carried out selectively on one carbonyl moiety. Also, the oximation of aldehydes over ketones has been accomplished successfully by this system.
- Setamdideh, Davood,Khezri, Behrooz,Esmaeilzadeh, Seyran
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p. 1119 - 1124
(2012/10/30)
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- PREPARATION OF CHIRAL AMIDES AND AMINES
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This invention provides a convenient method for converting oximes into enamides. The process does not require the use of metallic reagents. Accordingly, it produces the desired compounds without the concomitant production of a large volume of metallic waste. The enamides are useful precursors to amides and amines. The invention provides a process to convert a prochiral enamide into the corresponding chiral amide. In an exemplary process, a chiral amino center is introduced during hydrogenation through the use of a chiral hydrogenation catalyst. In selected embodiments, the invention provides methods of preparing amides and amines that include the 1,2,3,4-tetrahydro-N-alkyl-1-naphthalenamine or 1,2,3,4-tetrahydro-1-naphthalenamine substructure.
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Page/Page column 22
(2009/06/27)
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- A clean conversion of carbonyl compounds to oximes using silica gel supported hydroxylamine hydrochloride
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The efficient condensation of carbonyl compounds with hydroxylamine hydrochloride under solvent free conditions is described.
- Kiasat, Ali Reza,Kazemi, Foad,Nourbakhsh, Kazem
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p. 1193 - 1196
(2007/10/03)
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- A convenient one-pot method of converting alcohols into oximes
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The one-pot conversion of primary and secondary alcohols into oximes is reported using chromium trioxide supported on alumina and hydroxylamine hydrochloride under solvent free condition. This oxidation-oxime formation reaction has been applied to a range of aliphatic and benzylic alcohols.
- Kiasat, Ali Reza,Kazemi, Foad,Nourbakhsh, Kazem
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p. 1809 - 1812
(2007/10/03)
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- Application of aryloximes as solid-phase ketone linkers.
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In both solution and the solid phase, a variety of ketone oxime anions have been treated with 4-substituted-2-fluorobenzonitriles to give the corresponding nucleophilic aromatic substitution aryloxime adducts. Under aqueous acidic conditions, these adducts underwent cyclization to give the corresponding ketones. Suzuki and amide coupling reactions were also successfully performed on two resin-bound oximes followed by subsequent cyclorelease to give ketone product in good yields and purities. [reaction--see text]
- Lepore, Salvatore D,Wiley, Michael R
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- Novel guanidinobenzamides
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Compounds of formula IA and IB are new where the variables R1 through R10 have the values set forth herein. Such compounds have use in treating diseases such as obesity and type II diabetes, and may be provided as pharmaceutical form
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- Amberlyst A-21 an excellent heterogeneous catalyst for the conversion of carbonyl compounds to oximes
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Oximes can be efficiently obtained at room temperature by simply dissolving the appropriate carbonyl compounds and hydroxylamine hydrochloride, in ethanol, with Amberlyst A-21 as catalyst. Good yields of oximes are obtained, in very short reaction times, even with polifunctionalized substrates.
- Ballini, Roberto,Barboni, Luciano,Filippone, Paolino
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p. 475 - 476
(2007/10/03)
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- Stereoselective hydride reductions of cyclic N-diphenylphosphinyl imines. Highly diastereoselective syntheses of protected primary amines
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Reduction of N-diphenylphosphinyl imines of variously substituted cyclohexanones, cyclopentanones, and bicyclic ketones with lithium tri-sec-butylborohydride provides highly diastereoselective procedures for the syntheses of N-diphenylphosphinyl amines which represent protected primary amines that can be unmasked by mild acidic cleavage. Attack of cyclohexyl derivatives occurs almost exclusively via equatorial approach to yield axial amine derivatives while cyclopentyl and bicyclic imines are attacked from the less sterically encumbered faces.
- Hutchins,Adams,Rutledge
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p. 7396 - 7405
(2007/10/03)
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- 4'-Fluoro-4-{[4-(phenyl)cyclohexyl]amino}butyrophenones and the salts thereof
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This invention relates to novel 4-phenylcyclohexylamines embraced by the formula SPC1 Wherein ? is a generic expression denoting cis and trans stereoconfiguration and mixtures thereof; R is selected from the group consisting of alkyl of from one through four carbon atoms, fluorine, chlorine, bromine, trifluoromethyl, nitro and alkoxy of from one through four carbon atoms; R' and R1 are selected from the group consisting of hydrogen and alkyl of from one through four carbon atoms; R2 is selected from the group consisting of hydrogen, alkyl of from one through four carbon atoms, alkanoyl of from one through three carbon atoms, alkylsulfonyl of from one through three carbon atoms, arylsulfonyl of from six through ten carbon atoms, alkylcarbamoyl wherein alkyl is from one through four carbon atoms, alkoxycarbonyl wherein alkyl is from one through four carbon atoms, ring monosubstituted aroylalkyl wherein the substituents have the same meaning as R, above, aryl is from six through ten carbon atoms and alkyl is from one through six carbon atoms and bis (ring monosubstituted) arylalkyl wherein the substituents have the same meaning as R, above, aryl is from six through ten carbon atoms and alkyl is from one through six carbon atoms; R1 and R2 when taken together with --N is a saturated heterocyclic amino radical selected from the group consisting of unsubstituted and monosubstituted pyrrolidino, piperidino, hexamethylenimino, morpholino and piperazino; and an acid addition salt thereof. It also relates to intermediates and processes for the preparation of the aforesaid novel compounds (1) and novel derivatives thereof. The systemic administration to humans and animals of the novel compounds (1) depresses their central nervous systems.
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