53588-99-1Relevant academic research and scientific papers
A (1 R, 3 S) -3 - amino-cyclopentanol hydrochloride preparation method (by machine translation)
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, (2019/05/08)
The invention discloses a (1 R, 3 S) - 3 - amino-cyclopentanol hydrochloride of the preparation method, the method using chiral carboxylic acid with hydroxylamine to form the amide as chiral source, in copper catalyzed oxidation in the reaction system to rapidly obtain a chiral Diels - alder reaction product, after passes through the reduction reaction and alkaline deprotection reaction, and acidified after reaction to obtain the target product. Chiral inducing reagent chiral carboxylic acid by simple acidification, extraction processing can be reclaimed and reused. This kind of (1 R, 3 S) - 3 - amino-cyclopentanol hydrochloride preparation method has high operation safety and high selectivity, raw materials are easy, and the cost is low, the reaction time is short and simple process flow and the like. (by machine translation)
Diastereoselective Synthesis of Unnatural Amino Acids by Alkylation of α- Tert-Butanesulfinamide Auxiliary-Bound Enolates
Dwulet, Natalie C.,Zolfaghari, Tina A.,Brown, Molly L.,Cannon, Jeffrey S.
, p. 11510 - 11518 (2018/09/27)
A new chiral auxiliary for the diastereoselective alkylation of amino ester enolates that takes advantage of chiral information stored on the enolate side of the amino ester substrate has been developed. Chiral α-sulfinamido esters were alkylated under basic conditions in good yields (up to 90%) and good to high diastereoselectivities (generally >6:1) to provide unnatural mono- and α,α-disubstituted amino acid derivatives. This auxiliary allowed for the ready conversion of ester functionality without the need for esoteric reagents. Furthermore, the auxiliary is easily removed to provide enantiopure amino acids. Computational studies revealed that a chelated transition state governs electrophile addition from the convex face of a transient bicyclic intermediate. This method allows ready access to enantioenriched natural and unnatural amino acids.
Copper nanoparticles catalyzed N-H functionalization: An efficient solvent-free N-tert-butyloxycarbonylation strategy
Deb, Barnali,Debnath, Sudipto,Deb, Anindita,Maiti, Dilip K.,Majumdar, Swapan
supporting information, p. 629 - 633 (2017/01/25)
A chemoselective transformation of amines to their tert-butyloxycarbonyl (Boc) protected derivatives (NBoc) is described using Cu-NPs under solvent-free conditions. Simple method, rapid reaction rate, mild conditions, tolerance of a wide range of functional groups, excellent yield, ease recovery and high catalytic turnover are the salient features of this approach. tert-Butyloxycarbonylation of chiral amino acid esters and amino alcohols were performed without racemization.
Towards a universal organocatalyst for the synthesis of enantioenriched phenylalanine derivatives by enantioselective decarboxylative protonation
Pigeaux, Morgane,Laporte, Romain,Harrowven, David C.,Baudoux, Jér?me,Rouden, Jacques
, p. 4599 - 4603 (2016/09/23)
Access to enantioenriched non-proteogenic phenylalanine derivatives is described using the enantioselective decarboxylative protonation reaction of amidohemimalonate esters catalysed by various cinchona-based compounds. This study compares the catalytic efficiency as well as the enantioselectivity induced by three types of common organocatalysts, namely thioureas, squaramides and bis-cinchona squaramides. One of the main outcome of this work is the observation of a significant influence of the N-protecting group of the hemimalonate on its interaction with the catalyst. This methodology carried out under mild conditions exhibits good substrate scope and functional group tolerance. A substoichiometric amount of catalyst can also be used in certain cases while affording good yields and selectivities.
Symplocin A, a linear peptide from the bahamian cyanobacterium symploca sp. configurational analysis of N, N -dimethylamino acids by chiral-phase HPLC of naphthacyl esters
Molinski, Tadeusz F.,Reynolds, Kirk A.,Morinaka, Brandon I.
experimental part, p. 425 - 431 (2012/07/13)
The absolute stereostructures of the components of symplocin A (3), a new N,N-dimethyl-terminated peptide from the Bahamian cyanobacterium Symploca sp., were assigned from spectroscopic analysis, including MS, 2D NMR, and Marfey's analysis. The complete a
Selective esterifications of primary alcohols in a water-containing solvent
Wang, Yong,Aleiwi, Bilal A.,Wang, Qinghui,Kurosu, Michio
supporting information, p. 4910 - 4913,4 (2012/12/12)
Oxyma and an oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (5b), displayed a remarkable effect on selective esterifications of primary alcohols. A wide range of carboxylic acids could be esterified with primary alcohols by using EDCI, NaHCO3, and Oxyma or Oxyma derivative 5b in 5% H2O-CH3CN. Oxyma derivative 5b is particularly useful, since it could be removed after the reaction via a simple basic or an acidic aqueous workup procedure.
Selective esterifications of primary alcohols in a water-containing solvent
Wang, Yong,Aleiwi, Bilal A.,Wang, Qinghui,Kurosu, Michio
supporting information, p. 4910 - 4913 (2013/01/15)
Oxyma and an oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (5b), displayed a remarkable effect on selective esterifications of primary alcohols. A wide range of carboxylic acids could be esterified with primary alcohols by using EDCI, NaHCO3, and Oxyma or Oxyma derivative 5b in 5% H2O-CH3CN. Oxyma derivative 5b is particularly useful, since it could be removed after the reaction via a simple basic or an acidic aqueous workup procedure.
Double stereodifferentiation in the catalytic asymmetric aziridination of imines prepared from α-chiral amines
Huang, Li,Zhang, Yu,Staples, Richard J.,Huang, Rui H.,Wulff, William D.
, p. 5302 - 5313 (2012/05/20)
The catalytic asymmetric aziridination of imines and diazo compounds (AZ reaction) mediated by boroxinate catalysts derived from the VANOL and VAPOL ligands was investigated with chiral imines derived from five different chiral, disubstituted, methyl amines. The strongest matched and mismatched reactions with the two enantiomers of the catalyst were noted with disubstituted methyl amines that had one aromatic and one aliphatic substituent. The synthetic scope for the AZ reaction was examined in detail for α-methylbenzyl amine for cis-aziridines from α-diazo esters and for trans-aziridines from α-diazo acetamides. Optically pure aziridines could be routinely obtained in good yields and with high diastereoselectivity and the minor diastereomer (if any) could be easily separated. The matched case for cis-aziridines involved the (R)-amine with the (S)-ligand, but curiously, for trans-aziridines the matched case involved the (R)-amine with the (R)-ligand for imines derived from benzaldehyde and n-butanal, and the (R)-amine with the (S)-ligand for imines derived from the bulkier aliphatic aldehydes pivaldehyde and cyclohexane carboxaldehyde.
CHEMICAL COMPOUNDS
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Page/Page column 43, (2011/02/24)
The present invention relates to highly functionalized 1,3-diamino-propan-2-ols and pharmaceutically acceptable salts thereof. More specifically, the invention relates to highly functionalized 1,3-diamino-propan-2-ols that are derivatives of the HIV prote
An efficient and chemoselective Br?nsted acidic ionic liquid-catalyzed N-Boc protection of amines
Sunitha, Sadula,Kanjilal, Sanjit,Reddy, P. Srinivasa,Prasad, Rachapudi B.N.
, p. 2527 - 2532 (2008/09/19)
The first report of a Br?nsted acidic ionic liquid, 1-methylimidazolium tetrafluoroborate [(HMIm)BF4], catalyzed efficient and chemoselective N-Boc protection of various amines using (Boc)2O is presented. Optically pure amino alcohols and amino acid esters were converted efficiently to their corresponding optically pure N-Boc derivatives. The reported method is mild, solvent-free and has the advantages of both homogeneous and heterogeneous catalysis with high product yields, selectivity and ease of product separation.
