Enantioselective catalytic reduction of ketoimines with trichlorosilane promoted by readily available chiral Lewis bases.

Abstract:

:The straightforward synthesis of a series of enantiomerically pure Lewis basic amides by simple condensation of commercially available enantiopure diamines with picolinic acid is reported. These compounds were shown to promote the enantioselective reduction of ketoimines with trichlorosilane. Working with the model substrate N-phenyl benzophenone imine, the new organocatalysts led to the formation of the corresponding amine, with excellent chemical efficiency (up to 99% chemical yield) and good stereoselectivity (up to 73% ee). Up to 83% of enantioselectivity was reached in the reduction of differently substituted imines.

journal_name

Chirality

journal_title

Chirality

authors

Guizzetti S,Benaglia M,Cozzi F,Rossi S,Celentano G

doi

10.1002/chir.20615

subject

Has Abstract

pub_date

2009-01-01 00:00:00

pages

233-8

issue

1

eissn

0899-0042

issn

1520-636X

journal_volume

21

pub_type

杂志文章
  • Isolation and identification of sapotexanthin 5,6-epoxide and 5,8-epoxide from red mamey (Pouteria sapota).

    abstract::Two new carotenoids, sapotexanthin 5,6-epoxide and sapotexanthin 5,8-epoxide, have been isolated from the ripe fruits of red mamey (Pouteria sapota). Sapotexanthin 5,6-epoxide was also prepared by partial synthesis via epoxidation of sapotexanthin, and the (5R,6S) and (5S,6R) stereoisomers were identified by high-perf...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23206

    authors: Murillo E,Agócs A,Nagy V,Király SB,Kurtán T,Toribio EM,Lakey-Beitia J,Deli J

    更新日期:2020-05-01 00:00:00

  • Polymer-Supported Optically Active fac(S)-Tris(thiotato)rhodium(III) Complex for Sulfur-Bridging Reaction With Precious Metal Ions.

    abstract::The optically active mixed-ligand fac(S)-tris(thiolato)rhodium(III) complexes, ΔL -fac(S)-[Rh(aet)2 (L-cys-N,S)](-) (aet = 2-aminoethanethiolate, L-cys = L-cysteinate) () and ΔLL -fac(S)-[Rh(aet)(L-cys-N,S)2 ](2-) were newly prepared by the equatorial preference of the carboxyl group in the coordinated L-cys ligand. T...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22546

    authors: Aizawa S,Tsubosaka S

    更新日期:2016-01-01 00:00:00

  • Synthesis of molecularly imprinted polymers using a functionalized initiator for chiral-selective recognition of propranolol.

    abstract::We present a new concept of synthesis for preparation of molecularly imprinted polymers using a functionalized initiator to replace the traditional functional monomer. Using propranolol as a model template, a carboxyl-functionalized radical initiator was demonstrated to lead to high-selectivity polymer particles prepa...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.23167

    authors: Liu W,Holdsworth C,Ye L

    更新日期:2020-03-01 00:00:00

  • Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism.

    abstract::Advances in the measurement, calculation, and application of vibrational circular dichroism (VCD) for the determination of absolute configuration are described. The purpose of the review is to provide an up-to-date perspective on the capability of VCD to solve problems of absolute stereochemistry for chiral molecules ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10287

    authors: Freedman TB,Cao X,Dukor RK,Nafie LA

    更新日期:2003-11-01 00:00:00

  • Stereoselective kinetics of warfarin binding to human serum albumin: effect of an allosteric interaction.

    abstract::Kinetic and equilibrium binding studies were performed on the interaction of warfarin enantiomers with human serum albumin (HSA) in the absence and presence of lorazepam acetate (LoAc) enantiomers. Binding kinetics were followed by recording changes in the fluorescence of warfarin upon binding to HSA using the stopped...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10113

    authors: Fitos I,Visy J,Kardos J

    更新日期:2002-05-15 00:00:00

  • An improved synthesis of the enantiomers of BM-5 and their effects on the central in vivo release of acetylcholine.

    abstract::Racemic N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5), a putative postsynaptic agonist and presynaptic antagonist at muscarinic receptors, was resolved into the enantiomers by a new method suitable for large scale preparation. The method involves a chemoselective N-debenzylation as the key step. The en...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530040607

    authors: Nilsson BM,De Boer P,Grol CJ,Hacksell U

    更新日期:1992-01-01 00:00:00

  • Theoretical study of N-heterocyclic carbenes-catalyzed cascade annulation of benzodienones and enals.

    abstract::Growing attention in developing new N-heterocyclic carbene (NHC)-mediated reactions involving homoenolate intermediates has prompted our interest in exploring the mechanistic details of the related reactions. In this work, we carried out a detailed theoretical study for the NHC-catalyzed annulation reaction of cinnama...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22157

    authors: Sun H,Fang X,Chi YR,Li G

    更新日期:2013-09-01 00:00:00

  • Preparative and analytical separation of the zopiclone enantiomers and determination of their affinity to the benzodiazepine receptor binding site.

    abstract::We report the preparative separation of rac-zopiclone using malic acid as the resolving agent. Furthermore, two different methods for the analytical determination of zopiclone enantiomers by HPLC on chiral stationary phases are described. The benzodiazepine receptor binding of the isolated enantiomers was investigated...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530050605

    authors: Blaschke G,Hempel G,Müller WE

    更新日期:1993-01-01 00:00:00

  • Detection and quantification of (R) and (S)-dechloroethylifosfamide metabolites in plasma from children by enantioselective LC/MS/MS.

    abstract::Ifosfamide (IF), a potent chemotherapeutic agent for solid tumors, is known to cause high rates of nephrotoxicity in children with cancer, which is most likely due to the renal production of the metabolite chloroacetaldehyde. Using plasma samples obtained from pediatric oncology patients, we developed a simple nonderi...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20662

    authors: Aleksa K,Nava-Ocampo A,Koren G

    更新日期:2009-07-01 00:00:00

  • Separation of Enantiomers of a Phospholipid in Langmuir Monolayers by a New Selector.

    abstract::Chiral discrimination in a racemic mixture of dipalmitoylphosphatidylcholine (DPPC) is induced by a new selector at the water-air interface: L-DPPC is segregated in the condensed phase of a Langmuir monolayer upon interactions with an enantiopure amphiphilic compound. ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22508

    authors: Caminati G,Cicchi S,Lascialfari L,Brandi A

    更新日期:2015-11-01 00:00:00

  • Claisen-Schmidt condensation: Synthesis of (1S,6R)/(1R,6S)-2-oxo-N,4,6-triarylcyclohex-3-enecarboxamide derivatives with different substituents in H2 O/EtOH.

    abstract::A simple, green, and direct three-component condensation of acetophenone, aromatic aldehydes with 3-oxo-N-phenylbutanamide (acetoacetanilide) to generate some novel (1S,6R)/(1R,6S)-2-oxo-N,4,6-triarylcyclohex-3-enecarboxamide derivatives was carried out over K2 CO3 (10 mol%) with high efficiency in water/ethanol as gr...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22653

    authors: Mousavi SR

    更新日期:2016-11-01 00:00:00

  • Comparison of mid-infrared Fourier transform vibrational circular dichroism measurements with single and dual polarization modulations.

    abstract::Fourier transform infrared vibrational circular dichroism (FTIR-VCD) measurements have gone through major advances in the last decade. A major thrust in these advances was to find ways that can minimize the VCD spectral artifacts and obtain the VCD signals at enhanced signal quality. However, all these advances are no...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20999

    authors: Polavarapu PL,Shanmugam G

    更新日期:2011-10-01 00:00:00

  • Effect of serum lipoproteins on stereoselective halofantrine metabolism by rat hepatocytes.

    abstract::Experimental hyperlipidemia has shown to decrease cytochrome P450 3A4 and 2C11 expression and to increase liver concentrations and the plasma protein binding of halofantrine (HF) enantiomers. The present study examined the effect of hyperlipidemic (HL) serum on the metabolism of HF enantiomers by primary rat hepatocyt...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22054

    authors: Patel JP,Hamdy DA,El-Kadi AO,Brocks DR

    更新日期:2012-07-01 00:00:00

  • A systematic study of chiral homoprolinols and their derivatives in the catalysis of enantioselective addition of diethylzinc to aldehydes.

    abstract::Homoprolinol analogs, a class of optically active γ-amino alcohols, were examined systematically in the enantioselective addition reactions of diethylzinc to aldehydes. By comparison of the results catalyzed by these γ-amino alcohols with those by the β-amino alcohols based on pyrrolidine architecture reported in the ...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.21017

    authors: Liu CL,Wei CY,Wang SW,Peng YG

    更新日期:2011-11-01 00:00:00

  • Four conformers characterized in allyl nitrite.

    abstract::Allyl nitrite, O=NOCH(2)CH=CH(2), can exist in conformations which include syn (S) and anti (A) configurations of O=N-O-C, anti or gauche (G) configurations of N-O-C-C, and syn or skew (Sk) configurations of O-C-C=C. Four of them have been observed and characterized by their microwave spectra and quantum chemical calc...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.10065

    authors: Lee SG,Breeze L,Bohn RK,True NS

    更新日期:2002-02-01 00:00:00

  • Liquid chromatographic resolution of 3-amino-1,4-benzodiazepin-2-one derivatives on various Pirkle-type chiral stationary phases.

    abstract::The two enantiomers of N-acyl amide and N-ureide derivatives of 3-amino-5-phenyl-1,4-benzodiazepin-2-ones, which have been known to show anti-respiratory syncytial virus (RSV) activity, were resolved on seven different Pirkle-type chiral stationary phases (CSPs) with the use of 10% isopropyl alcohol in hexane as a mob...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20944

    authors: Park JY,Cho HS,Hyun MH

    更新日期:2011-01-01 00:00:00

  • C3-symmetrical self-assembled structures investigated by vibrational circular dichroism.

    abstract::We demonstrate by using vibrational circular dichroism (VCD) spectroscopy that it is possible to investigate the chirality of a supramolecular polymeric system in relatively dilute solutions. Chiral C(3)-symmetrical discotic molecules, based on a trialkylbenzene-1,3,5-carboxamide, form supramolecular columnar stacks w...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20568

    authors: Smulders MM,Buffeteau T,Cavagnat D,Wolffs M,Schenning AP,Meijer EW

    更新日期:2008-09-01 00:00:00

  • Discrimination in resolving systems: ephedrine-mandelic acid.

    abstract::Resolution of mandelic acid with (-)-(1R,2S)-ephedrine in water and ethanol produces intermediate diastereomeric salts with greatly disparate solubilities and melting points. Single crystal X-ray analysis of the less (L) and more (M) soluble (-)-ephedrinium mandelates (I, II) shows crystal structures which are isoster...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.530040807

    authors: Valente EJ,Zubkowski J,Eggleston DS

    更新日期:1992-01-01 00:00:00

  • Stereolability of chiral ruthenium catalysts with frozen NHC ligand conformations investigated by dynamic-HPLC.

    abstract::The stereolability of chiral Hoveyda-Grubbs II type ruthenium complexes bearing N-heterocyclic carbene (NHC) ligands with Syn-phenyl groups on the backbone and Syn- or Anti-oriented o-tolyl N-substituents was studied by resorting to dynamic high-performance liquid chromatography (D-HPLC). A complete chromatographic pi...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22487

    authors: Menta S,Pierini M,Cirilli R,Grisi F,Perfetto A,Ciogli A

    更新日期:2015-10-01 00:00:00

  • A colorimetric chiral sensor based on chiral crown ether for the recognition of the two enantiomers of primary amino alcohols and amines.

    abstract::A new colorimetric chiral sensor material consisting of three different functional sites such as chromophore (2,4-dinitrophenylazophenol dye), binding site (crown ether), and chiral barrier (3,3'-diphenyl-1,1'-binaphthyl group) was prepared and applied to the recognition of the two enantiomers of primary amino alcohol...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20928

    authors: Cho EN,Li Y,Kim HJ,Hyun MH

    更新日期:2011-04-01 00:00:00

  • Excitatory amino acid receptor antagonists: resolution, absolute stereochemistry, and pharmacology of (S)- and (R)-2-amino-2-(5-tert-butyl-3-hydroxyisoxazol-4-yl)acetic acid (ATAA).

    abstract::We have previously shown that (RS)-2-amino-2-(5-tert-butyl-3-hydroxyisoxazol-4-yl)acetic acid (ATAA) is an antagonist at N-methyl-D-aspartic acid (NMDA) and (RS)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid (AMPA) receptors. We have now resolved ATAA via diastereomeric salt formation using N-BOC protected...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(1997)9:5/6<529::AID-CHIR20

    authors: Johansen TN,Frydenvang K,Ebert B,Madsen U,Krogsgaard-Larsen P

    更新日期:1997-01-01 00:00:00

  • Determination of the absolute configuration and solution conformation of a novel disubstituted pyrrolidine acid A by vibrational circular dichroism.

    abstract::Compound A, a novel disubstituted pyrrolidine acid, is a member of a new class of agents that are potentially useful for the treatment of diabetes and dyslipidemia. The absolute configuration of this compound was determined by using vibrational circular dichroism (VCD). The results are in agreement with the assignment...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20316

    authors: Freedman TB,Cao X,Phillips LM,Cheng PT,Dalterio R,Shu YZ,Zhang H,Zhao N,Shukla RB,Tymiak A,Gozo SK,Nafie LA,Gougoutas JZ

    更新日期:2006-09-01 00:00:00

  • Structure and unexpected chiroptical properties of chiral 4-pyrrolidinyl substituted 2(5H)-furanones.

    abstract::Planar 2(5H)-furanones substituted at C4 with a chiral pyrrolidinyl group show CD spectra which are apparently due to the distortion of the C4-N1 bond of sp2 character from the plane defined by the 2(5H)-furanone ring atoms and/or due to the presence of substituents in the pyrrolidine ring. This is a new, previously n...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20059

    authors: Gawroński J,Gawrońska K,Kwit M,Kacprzak K,Rychlewska U

    更新日期:2004-08-01 00:00:00

  • A new definition of life.

    abstract::Chirality is often glossed over in theoretical or experimental discussions concerning the origin of life, but the ubiquity of homochiral building blocks in known biological systems demands explanation. Information theory can provide a quantitative framework for understanding the role of chirality in biology. Here I sh...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20590

    authors: Carroll JD

    更新日期:2009-03-01 00:00:00

  • Screening Approach for Chiral Separation of β-Aminoketones by HPLC on Various Polysaccharide-Based Chiral Stationary Phases.

    abstract::Nine β-aminoketones were synthesized via Mannich reaction when benzaldehyde was condensed with some primary amines and acetophenone. The purified compounds were identified by using spectroscopic methods. The enantiomeric separation of these derivatives was carried out by high-performance liquid chromatography (HPLC) u...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22434

    authors: Addadi K,Sekkoum K,Belboukhari N,Cheriti A,Aboul-Enein HY

    更新日期:2015-05-01 00:00:00

  • Absolute stereochemistry of unusual biopolymers from Ascomycete culture LL-W1278: examples that derivatives of (S)-6-hydroxymellein are also natural fungal metabolites.

    abstract::The new linear polyesters, W1278-A, B, and C, were isolated from culture extracts of a freshwater Ascomycete fungus. Their structures were elucidated on the basis of spectroscopic analyses and chemical transformations, with the absolute configuration established by the circular dichroism (CD) method using (R)-(-)-6-hy...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20105

    authors: Schlingmann G,Roll DM

    更新日期:2005-01-01 00:00:00

  • NMR studies of dextromethorphan in both isotropic and anisotropic states.

    abstract::Herein, we present the solution-state NMR studies on dextromethorphan (1) under both isotropic and anisotropic conditions. From the measurement of 22 residual dipolar couplings using a stretched polystyrene gel (PS), we show that accurate and detailed structural information is readily determined including the relative...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.20703

    authors: Swarbrick JD,Ashton TD

    更新日期:2010-01-01 00:00:00

  • Chiroptical studies on supramolecular chirality of molecular aggregates.

    abstract::The attempts of applying chiroptical spectroscopy to supramolecular chirality are reviewed with a focus on vibrational circular dichroism (VCD). Examples were taken from gels, solids, and monolayers formed by low-molecular mass weight chiral gelators. Particular attention was paid to a group of gelators with perfluoro...

    journal_title:Chirality

    pub_type: 杂志文章,评审

    doi:10.1002/chir.22482

    authors: Sato H,Yajima T,Yamagishi A

    更新日期:2015-10-01 00:00:00

  • Unprecedented crystallization and X-ray crystal structure of racemic N(alpha)-(t-butyloxycarbonyl)-L-L-phenylalanine N-methoxy-N-methylamide.

    abstract::Weinreb amide 3 was synthesized using isobutyl chloroformate, carbonyldiimidazole, or ethylcarbodiimide as the coupling agent in the reaction of Boc-phenylalanine with O,N-dimethylhydroxylamine hydrochloride. An optically active oil was isolated along with an optically inactive solid irrespective of the type of coupli...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/(SICI)1520-636X(2000)12:1<2::AID-CHIR2>3.0

    authors: Zheng X,Donkor IO,Miller DD,Ross CR 2nd

    更新日期:2000-01-01 00:00:00

  • Molecular enantiorecognition of l-glucose and d-glucose in whole blood samples.

    abstract::In the past years, enantioanalysis became very important for clinical analysis; biomarkers/substances of biomedical importance with chiral structure should be analyzed and their presence correlated with the specific disorder. Therefore, we developed a method for the assay of l- and d-glucose, based on molecular recogn...

    journal_title:Chirality

    pub_type: 杂志文章

    doi:10.1002/chir.22843

    authors: Stefan-van Staden RI,Mitrofan G

    更新日期:2018-05-01 00:00:00