19144-86-6Relevant articles and documents
Solvent-induced chirality control in the enantioseparation of 1-phenylethylamine via diastereomeric salt formation
Kodama, Koichi,Kimura, Yuria,Shitara, Hiroaki,Yasutake, Mikio,Sakurai, Rumiko,Hirose, Takuji
, p. 326 - 332 (2011)
Solvent-induced chirality control in the enantioseparation of 1-phenylethylamine 1 by N-(p-toluenesulfonyl)-(S)-phenylalanine 2 via diastereomeric salt formation was studied. (S)-·(S)-2 was preferentially crystallized as a less-soluble salt from aqueous a
Ph-tetrame-bithienine, the first member of the class of chiral heterophosphepines: Synthesis, electronic and steric properties, metal complexes and catalytic activity
Vaghi, Luca,Benincori, Tiziana,Cirilli, Roberto,Alberico, Elisabetta,Mussini, Patrizia Romana,Pierini, Marco,Pilati, Tullio,Rizzo, Simona,Sannicolo, Francesco
, p. 8174 - 8184 (2013)
Unknown 1H-2,7-dihydro-1-phenylphosphepine, containing a 2,2,5,5-tetramethyl-3,3-bithiophene atropisomeric scaffold (Ph-tetraMe- Bithienine), and its oxide have been synthesized and structurally characterized by single-crystal X-ray diffraction analysis.
Unprecedented, fully recyclable, solid-supported reagent for the kinetic resolution of racemic amines through enantioselective N-acetylation
Arseniyadis, Stellios,Subhash, Pithani V.,Valleix, Alain,Wagner, Alain,Mioskowski, Charles
, p. 3310 - 3312 (2005)
The high-yielding synthesis and application of the first polymer supported reagent for the kinetic resolution (KR) of amines through enantioselective acetylation is described; this new supported chiral reagent allows the KR of primary amines with excellent selectivities at room temperature; moreover, this supported approach is highly efficient as the Merrifield-supported chiral scaffold can be quantitatively recovered and recycled. The Royal Society of Chemistry 2005.
A new benchmark for the non-enzymatic enantioselective acylation of amines: Use of a planar-chiral derivative of 4-pyrrolidinopyridine as the acylating agent
Ie, Yutaka,Fu, Gregory C.
, p. 119 - 120 (2000)
N-Acetylated Ph-PPY*, a new planar-chiral derivative of PPY, serves as an effective reagent for the enantioselective acylation of racemic amines, providing amides with very good stereoselectivity.
Rhodium-catalyzed asymmetric olefin hydrogenation by easily accessible aniline- and pyridine-derived chiral phosphites
Vallianatou, Kalliopi A.,Frank, Dominik J.,Antonopoulou, Georgia,Georgakopoulos, Spyros,Siapi, Eleni,Zervou, Maria,Kostas, Ioannis D.
, p. 397 - 401 (2013)
An aniline- and two pyridine-derived (R)-BINOL-based P,N-containing phosphite ligands have been synthesized via a one-pot procedure. Treatment of the aniline-derived ligand with 1 equiv of [Rh(COD)2]BF4 yielded a mixture of a P,N-che
Asymmetric Induction via Co-ordination to Cr(CO)3; Nucleophilic Attack on Acyclic Carbenium Ions
Top, Siden,Jaouen, Gerard,McGlinchey, Michael J.
, p. 1110 - 1112 (1980)
Temporary complexation of (S)-(-)-1-phenylethanol by the Cr(CO)3 moiety allows the use of carbenium ions to bring about asymmetric transformations with a high degree of retention of configuration, even in open-chain compounds.
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Tsuchihashi,G. et al.
, p. 3389 - 3392 (1973)
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Potential application of native lipases in the resolution of (RS)-phenylethylamine
Pilissa?o, Cristiane,De O. Carvalho, Patri?cia,Da G. Nascimento, Maria
, p. 973 - 977 (2010)
The performance of two native lipases (lipase from Aspergillus niger and Rhizoupus oligosporus) in the resolution of (RS)-phenylethylamine (1), varying the temperature, acyl donor type (ethyl acetate, vinyl acetate, iso-propenyl acetate and acetic anhydride) and organic medium, was studied. The effect of the nature of the anion using native A. niger lipase in n-heptane with a series of imidazolium-based ILs [BMIm][X], where X = BF4, PF6, SCN and Cl, was also evaluated. Using the lipase from A. niger, the R-2b amide was obtained with conversions from 6 to > 99percent and E-values from 2 to > 200, with n-heptane or n-hexane. This lipase showed better E-values in a two-phase system using n-heptane and [BMIm][PF6] or [BMIm][BF4] 9:1 (v/v), obtaining values of 9 and 7, respectively, when vinyl acetate was used as the acyl donor, compared to the use of pure n-heptane (E = 2). The series for the anions in terms of decreasing performance was as follows: PF 6->BF4-> SCN-> Cl-.
Synthesis and crystal structure of enantiomeric N-(dimethylfluorosilylmethyl) and N-(dimethylchlorosilylmethyl)-[N-( S) -1-phenylethyl ] acetamides
Baukov, Yuri I.,Ovchinnikov, Yuri E.,Shipov, Aleksandr G.,Kramarova, Evgeniya P.,Negrebetsky, Vadim V.,Struchkov, Yuri T.
, p. 399 - 403 (1997)
Synthesis of the first optically active compounds containing asymmetric carbon and pentacoordinated silicon has been carried out. The enantiomeric (O-Si)-chelate N-(dimethylhalogenosilylmethyl) acetamides, MeC(O)N(CH(Ph)Me)CH2SiMe2X
Enantioconvergent Cu-Catalyzed Radical C-N Coupling of Racemic Secondary Alkyl Halides to Access α-Chiral Primary Amines
Cheng, Jiang-Tao,Dong, Xiao-Yang,Gu, Qiang-Shuai,Li, Zhong-Liang,Liu, Juan,Liu, Xin-Yuan,Luan, Cheng,Wang, Fu-Li,Wang, Li-Lei,Yang, Ning-Yuan,Zhang, Yu-Feng
supporting information, p. 15413 - 15419 (2021/09/30)
α-Chiral alkyl primary amines are virtually universal synthetic precursors for all other α-chiral N-containing compounds ubiquitous in biological, pharmaceutical, and material sciences. The enantioselective amination of common alkyl halides with ammonia is appealing for potential rapid access to α-chiral primary amines, but has hitherto remained rare due to the multifaceted difficulties in using ammonia and the underdeveloped C(sp3)-N coupling. Here we demonstrate sulfoximines as excellent ammonia surrogates for enantioconvergent radical C-N coupling with diverse racemic secondary alkyl halides (>60 examples) by copper catalysis under mild thermal conditions. The reaction efficiently provides highly enantioenrichedN-alkyl sulfoximines (up to 99% yield and >99% ee) featuring secondary benzyl, propargyl, α-carbonyl alkyl, and α-cyano alkyl stereocenters. In addition, we have converted the masked α-chiral primary amines thus obtained to various synthetic building blocks, ligands, and drugs possessing α-chiral N-functionalities, such as carbamate, carboxylamide, secondary and tertiary amine, and oxazoline, with commonly seen α-substitution patterns. These results shine light on the potential of enantioconvergent radical cross-coupling as a general chiral carbon-heteroatom formation strategy.
Chiral ferrocene phosphine-indole aminophosphine ligand as well as preparation method and application thereof
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Paragraph 0048-0049, (2021/05/22)
The invention discloses a chiral ferrocene phosphine-indole aminophosphine ligand as well as a preparation method and application thereof. The preparation method comprises the following steps: dissolving a chiral ferrocene phosphine-indole intermediate in
Environmentally benign decarboxylative: N-, O-, and S-Acetylations and acylations
Ghosh, Santanu,Purkait, Anisha,Jana, Chandan K.
supporting information, p. 8721 - 8727 (2020/12/30)
An operationally simple and general method for acetylation and acylation of a wide variety of substrates (amines, alcohols, phenols, thiols, and hydrazones) has been reported. Meldrum's acid and its derivatives have been used as an air-stable, non-volatile, cost-effective, and easy to handle acetylating/acylating agent. Easily separable byproducts (CO2 and acetone) allowed the isolation of analytically pure acetylated products without the requirement of work-up and any chromatography. This journal is