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Search for "asymmetric organocatalysis" in Full Text gives 35 result(s) in Beilstein Journal of Organic Chemistry.

Recent advances in organocatalytic atroposelective reactions

  • Henrich Szabados and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

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  • becoming increasingly relevant also in medicine. Many axially chiral compounds are important as catalysts in asymmetric catalysis or have chiroptical properties. This review overviews recent progress in the synthesis of axially chiral compounds via asymmetric organocatalysis. Atroposelective
  • acids feature as the most prolific catalytic structure. The last part of the article discusses hydrogen-bond-donating catalysts and other catalyst motifs such as phase-transfer catalysts. Keywords: asymmetric organocatalysis; atropoisomers; atroposelective synthesis; axial chirality; stereogenic axis
  • organocatalyzed, methods [7][8][9][10][11]. Asymmetric organocatalysis offers efficient and environmentally benign access to numerous chiral compounds [12]. Therefore, an increasing number of researchers are now investigating the organocatalytic formation of compounds with axial stereogenic axes across various
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Published 09 Jan 2025

Non-covalent organocatalyzed enantioselective cyclization reactions of α,β-unsaturated imines

  • Sergio Torres-Oya and
  • Mercedes Zurro

Beilstein J. Org. Chem. 2024, 20, 3221–3255, doi:10.3762/bjoc.20.268

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  • imines; asymmetric organocatalysis; cyclization; N-heterocycles; inverse electron demand aza-Diels–Alder reaction; Introduction Nitrogen-containing heterocycles are abundant scaffolds present in natural products, biologically active compounds, pharmaceuticals, synthetic agrochemicals, and functional
  • , and it will be a useful reference for organic chemists working in the field of asymmetric organocatalysis. The review is divided into sections, each covering a different catalytic system. Additionally, a chronological order is followed in the subchapters. In order to also give a general overview of
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Published 10 Dec 2024

Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis

  • Stefan P. Schmid,
  • Leon Schlosser,
  • Frank Glorius and
  • Kjell Jorner

Beilstein J. Org. Chem. 2024, 20, 2280–2304, doi:10.3762/bjoc.20.196

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  • the award of the Nobel Prize to List and MacMillan in 2021 ‘for the development of asymmetric organocatalysis’. Organocatalytic transformations have also seen the transition to industrial processes for the production of a variety of pesticides and medicinal compounds, as recently reviewed [6][7][8][9
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Published 10 Sep 2024

Factors influencing the performance of organocatalysts immobilised on solid supports: A review

  • Zsuzsanna Fehér,
  • Dóra Richter,
  • Gyula Dargó and
  • József Kupai

Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183

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  • MacMillan were awarded the Nobel Prize in 2021 for the development of asymmetric organocatalysis [6]. To date, industrial companies have used a number of asymmetric organocatalytic processes to synthesise pharmaceuticals and fine chemicals on large scales [7]. Catalyst recycling is key from both an economic
  • has organic building blocks, both condensation [98] and post-synthetic modification [99] methods can be used to immobilise organocatalysts. Asymmetric organocatalysis is commonly achieved by pyrrolidone ligands, with great results in a variety of reactions, such as Michael [100] and aldol [101
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Published 26 Aug 2024

Chiral phosphoric acid-catalyzed transfer hydrogenation of 3,3-difluoro-3H-indoles

  • Yumei Wang,
  • Guangzhu Wang,
  • Yanping Zhu and
  • Kaiwu Dong

Beilstein J. Org. Chem. 2024, 20, 205–211, doi:10.3762/bjoc.20.20

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  • excellent yield and enantioselectivity. Keywords: asymmetric organocatalysis; chiral Brønsted acid; 3,3-difluoroindoline; Hantzsch ester; transfer hydrogenation; Introduction The introduction of fluoro atoms into organic molecules can alter their lipophilicity, solubility, metabolic stability, and
  • relatively strict reaction conditions (up to 150 bar H2). In 2022, Liu’s group reported an asymmetric hydrogenation of 3H-indoles catalyzed by a chiral Mn complex, which showed good yield and enantioselectivity [25]. In addition to metal catalysis for the enantioselective reduction, asymmetric
  • organocatalysis using chiral phosphoric acids has also been studied (Scheme 1b) [26][27][28]. In 2010, Magnus Rueping and his co-workers developped an enantioselective Brønsted acid-catalyzed transfer hydrogenation of 3H-indoles [29]. In 2020, Song and Yu successfully applied a new chiral Brønsted acid
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Letter
Published 01 Feb 2024

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

  • Gyula Dargó,
  • Dóra Erdélyi,
  • Balázs Molnár,
  • Péter Kisszékelyi,
  • Zsófia Garádi and
  • József Kupai

Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133

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  • processes are of paramount importance. In particular, the application of asymmetric organocatalysts is receiving increased attention [1][2][3][4]. This is illustrated by the fact that in 2021 the Nobel Prize in Chemistry was awarded for the discovery of asymmetric organocatalysis [5]. The use of
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Published 24 Nov 2023
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  • acyclic, carbocyclic, heterocyclic, and polycyclic molecular architectures with high molecular complexity. In particular, asymmetric organocatalysis plays a pivotal role in the construction of optically active, bioactive, and natural products. The main advantages of organocatalyzed stereoselective
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Published 28 Jun 2023

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

  • Elena R. Lopat’eva,
  • Igor B. Krylov,
  • Dmitry A. Lapshin and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

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  • redox-neutral asymmetric organocatalysis, whereas organocatalysis by redox-active molecules stays in the shadows. For example, redox-active organic molecules are almost not mentioned in some recent overviews of compound types used in organocatalysis [3][12][13], except for photoredox catalysts [12][13
  • organocatalysis in general. Examples of typical reaction types for redox-neutral asymmetric organocatalysis are aldol reactions [13], Michael reactions [14][15][16], and Diels–Alder reactions [17][18]. The processes associated with changing oxidation states of atoms in substrates thus can be named “redox
  • play an important role in redox-neutral asymmetric organocatalysis by forming nucleophilic enamine intermediates or electrophilic iminium cations. The same principles are used in oxidative transformations, where an amine can play the role of chirality source and the activator of substrate for oxidation
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Perspective
Published 09 Dec 2022

Design, synthesis, and evaluation of chiral thiophosphorus acids as organocatalysts

  • Karen R. Winters and
  • Jean-Luc Montchamp

Beilstein J. Org. Chem. 2022, 18, 1471–1478, doi:10.3762/bjoc.18.154

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  • asymmetric organocatalysis. In order to eliminate the need for C2-symmetry in common CPAs, various scaffolds containing C1-symmetrical thiophosphorus acids were chosen. These new compounds were synthesized and evaluated in the asymmetric transfer hydrogenation of 2-phenylquinoline. Although the efficacy of
  • the thiophosphorus acids was disappointing for this reaction, the work should be useful for developing structural design elements. Keywords: asymmetric; heterocycles; organocatalysis; phosphorus; synthesis; Introduction The importance of asymmetric organocatalysis was demonstrated by the 2021 Nobel
  • SPINOL [4][5] (Figure 1). The great success of these CPAs in asymmetric organocatalysis, is demonstrated by the publication of thousands of articles and reviews [6][7][8][9][10][11][12][13][14][15][16][17]. In all cases the C2-symmetry is required because of the prototropic tautomeric equilibrium in the
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Published 17 Oct 2022

New advances in asymmetric organocatalysis

  • Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 240–242, doi:10.3762/bjoc.18.28

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  • Radovan Sebesta Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia 10.3762/bjoc.18.28 Keywords: asymmetric organocatalysis; covalent activation; noncovalent activation; Asymmetric catalysis is
  • organocatalysis edited by one of the pioneers Benjamin List. After another decade, this thematic issue likes to survey new advances in this field. Three review articles and nine research papers showcase the diversity and breadth into which asymmetric organocatalysis has grown since then. The suitability of
  • many reactions and a variety of organocatalysts can engage with them [18]. Nine excellent research articles within this special issue demonstrate the current state of the art in asymmetric organocatalysis. Chiral isothioureas became useful Lewis base catalysts for various transformations. Weinzierl and
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Editorial
Published 28 Feb 2022

N-Sulfinylpyrrolidine-containing ureas and thioureas as bifunctional organocatalysts

  • Viera Poláčková,
  • Dominika Krištofíková,
  • Boglárka Némethová,
  • Renata Górová,
  • Mária Mečiarová and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2021, 17, 2629–2641, doi:10.3762/bjoc.17.176

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  • aldehydes and hydrogen-bond activation of nitroalkenes. Keywords: asymmetric organocatalysis; hydrogen bond; Michael addition; pyrrolidine; thiourea; urea; Introduction Asymmetric organocatalysis became one of the strategic ways for the efficient synthesis of chiral compounds [1]. Bifunctional catalysis
  • has proven to be a successful concept in asymmetric organocatalysis [2][3][4][5][6][7][8]. An amine unit with a hydrogen-bond donating skeleton is highly efficient from among various possible combinations of catalytic moieties within an organocatalyst. This idea has been inspired by proline catalysis
  • /mismatched combination of chirality, we employed both enantiomers of tert-butyl sulfinamide with the (S)-enantiomer of the pyrrolidine building block. The introduction of green chemistry principles into chemical transformations is an important goal toward sustainable production and manufacturing. Asymmetric
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Published 25 Oct 2021

Asymmetric organocatalyzed synthesis of coumarin derivatives

  • Natália M. Moreira,
  • Lorena S. R. Martelli and
  • Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

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  • a specific target, i.e., it gives access to a greater diversity of compounds to be explored [26]. In this work, a compilation of the enantioselective synthesis of coumarin derivatives using asymmetric organocatalysis is presented, highlighting the proposed mechanism pathways for the formation of the
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Published 03 Aug 2021

Asymmetric synthesis of CF2-functionalized aziridines by combined strong Brønsted acid catalysis

  • Xing-Fa Tan,
  • Fa-Guang Zhang and
  • Jun-An Ma

Beilstein J. Org. Chem. 2020, 16, 638–644, doi:10.3762/bjoc.16.60

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  • no enantioselectivity at all. As arylboronic acids have been harnessed to enhance the Brønsted acidity in asymmetric organocatalysis in combination with chiral diols or chiral aminoalcohols [40][41][42][43][44], we envisioned that the simultaneous use of arylboronic acids and chiral Brønsted acids
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Published 07 Apr 2020

Catalytic asymmetric oxo-Diels–Alder reactions with chiral atropisomeric biphenyl diols

  • Chi-Tung Yeung,
  • Wesley Ting Kwok Chan,
  • Wai-Sum Lo,
  • Ga-Lai Law and
  • Wing-Tak Wong

Beilstein J. Org. Chem. 2019, 15, 955–962, doi:10.3762/bjoc.15.92

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  • : asymmetric organocatalysis; axial chirality; biaryls; hydrogen bond; oxo-Diels–Alder reaction; Introduction The Diels–Alder (DA) reaction is a useful and easy-to-perform method for the synthesis of six-membered rings through the direct formation of C–C bonds between a diene and a dienophile (a substituted
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Published 18 Apr 2019

New α- and β-cyclodextrin derivatives with cinchona alkaloids used in asymmetric organocatalytic reactions

  • Iveta Chena Tichá,
  • Simona Hybelbauerová and
  • Jindřich Jindřich

Beilstein J. Org. Chem. 2019, 15, 830–839, doi:10.3762/bjoc.15.80

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  • others [24]. Hence, combining cinchona alkaloids with CDs has the potential to widen the applications of CD derivatives in asymmetric organocatalysis. The combination of cinchona alkaloids with CDs was first reported by Liu et al. [25] who prepared inclusion complexes of cinchona alkaloids and
  • alkaloids have never been prepared and tested in asymmetric organocatalysis. Thus, in this study, we investigated methods for attaching cinchona alkaloids to CD skeletons, and we assessed the enantiomeric excess of the resulting CD derivatives as organocatalysts in asymmetric reactions, specifically in the
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Published 01 Apr 2019

Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives

  • Zheng-Yi Li,
  • Hong-Xiao Tong,
  • Yuan Chen,
  • Hong-Kui Su,
  • Tangxin Xiao,
  • Xiao-Qiang Sun and
  • Leyong Wang

Beilstein J. Org. Chem. 2018, 14, 1901–1907, doi:10.3762/bjoc.14.164

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  • During the past decades, asymmetric organocatalysis has played an important role as a tool for the syntheses of chiral molecules under mild conditions [1][2][3][4]. Among these reactions, the asymmetric Michael reaction is a powerful strategy to construct versatile intermediates due to its synthetic
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Published 25 Jul 2018

Recent applications of chiral calixarenes in asymmetric catalysis

  • Mustafa Durmaz,
  • Erkan Halay and
  • Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

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  • rim have been successfully developed and used in chiral recognition. But their use in asymmetric organocatalysis hasn’t been reported. To explore the organocatalytic behaviors of inherently chiral calix[4]arenes modified at the lower rim, Li et al. reported the synthesis of N,O-type enantiomers based
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Published 08 Jun 2018

Diastereoselective auxiliary- and catalyst-controlled intramolecular aza-Michael reaction for the elaboration of enantioenriched 3-substituted isoindolinones. Application to the synthesis of a new pazinaclone analogue

  • Romain Sallio,
  • Stéphane Lebrun,
  • Frédéric Capet,
  • Francine Agbossou-Niedercorn,
  • Christophe Michon and
  • Eric Deniau

Beilstein J. Org. Chem. 2018, 14, 593–602, doi:10.3762/bjoc.14.46

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  • provide 3-substituted isoindolinones in good yields and diastereomeric excesses. This methodology was applied to the asymmetric synthesis of a new pazinaclone analogue which is of interest in the field of benzodiazepine-receptor agonists. Keywords: asymmetric organocatalysis; Aza-Michael reaction; phase
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Published 09 Mar 2018

Investigations towards the stereoselective organocatalyzed Michael addition of dimethyl malonate to a racemic nitroalkene: possible route to the 4-methylpregabalin core structure

  • Denisa Vargová,
  • Rastislav Baran and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2018, 14, 553–559, doi:10.3762/bjoc.14.42

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  • catalyst. Furthermore, specific organocatalysts can provide respective stereoisomers of the key Michael adduct in up to 99:1 er. Keywords: kinetic resolution; Michael addition; organocatalysis; pregabalin; squaramide; Introduction Asymmetric organocatalysis has considerably broadened possibilities for
  • amino acids have also been investigated as treatments for ocular disorders [7]. However, the syntheses of this type of compounds were long and relied on the use of Evans chiral auxiliaries or chiral starting materials. Various GABA derivatives were synthesized using asymmetric organocatalysis
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Published 05 Mar 2018

Chiral phase-transfer catalysis in the asymmetric α-heterofunctionalization of prochiral nucleophiles

  • Johannes Schörgenhumer,
  • Maximilian Tiffner and
  • Mario Waser

Beilstein J. Org. Chem. 2017, 13, 1753–1769, doi:10.3762/bjoc.13.170

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  • strategy. Hereby both, approaches relying on either asymmetric metal- or organocatalysis, have been well-investigated already [105][106][107][108][109][110][111][112][113][114][115][116][117][118][119][120][121][122]. In the field of non-covalent asymmetric organocatalysis, chiral H-bonding catalysis [37
  • -transfer reactions is hydrogen peroxide (H2O2). Unfortunately, the direct use of this base-chemical under asymmetric organocatalysis turned out to be rather tricky for α-hydroxylation reactions. One recent report by the Ooi group overcame some of the limitations by using H2O2 in combination with
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Published 22 Aug 2017

Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

  • Pierre Querard,
  • Inna Perepichka,
  • Eli Zysman-Colman and
  • Chao-Jun Li

Beilstein J. Org. Chem. 2016, 12, 2636–2643, doi:10.3762/bjoc.12.260

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  • of THIQs with arylboronic esters via asymmetric organocatalysis methodology [25][28]. The use of chiral tartaric acid derivatives, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and high temperature (70 °C) were found to be the optimal conditions to obtain the desired arylated product with
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Published 06 Dec 2016

Highly chemo-, enantio-, and diastereoselective [4 + 2] cycloaddition of 5H-thiazol-4-ones with N-itaconimides

  • Shuai Qiu,
  • Choon-Hong Tan and
  • Zhiyong Jiang

Beilstein J. Org. Chem. 2016, 12, 2293–2297, doi:10.3762/bjoc.12.222

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  • ) were obtained for a series of spirocyclic 1,4-sulfur-bridged piperidinone-based succinimides. Keywords: [4 + 2] annulation; asymmetric organocatalysis; dipeptide-based Brønsted bases; 5H-thiazol-4-ones; N-itaconimides; Introduction Sulfur-containing tetrasubstituted carbon stereocenters are widely
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Published 01 Nov 2016

Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

  • Bin Yu,
  • Hui Xing,
  • De-Quan Yu and
  • Hong-Min Liu

Beilstein J. Org. Chem. 2016, 12, 1000–1039, doi:10.3762/bjoc.12.98

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  • have been developed and used in the synthesis of natural products and pharmaceutical agents. Biologically important 3-hydroxyoxindoles with a chiral quaternary center at the 3-position have been successfully accessed utilizing the asymmetric organocatalysis in the last few years. To show recent
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Published 18 May 2016

Asymmetric α-amination of 3-substituted oxindoles using chiral bifunctional phosphine catalysts

  • Qiao-Wen Jin,
  • Zhuo Chai,
  • You-Ming Huang,
  • Gang Zou and
  • Gang Zhao

Beilstein J. Org. Chem. 2016, 12, 725–731, doi:10.3762/bjoc.12.72

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  • tetrasubstituted carbon center have been recognized as core building blocks for the preparation of many biologically active and therapeutic compounds [2][3][4][5][6][7]. As a type of commercially available electrophilic amination reagents, azodicarboxylates have been extensively used in both asymmetric
  • organocatalysis and metal catalysis for the construction of this type of structures. For example, Chen et al. reported the first organocatalytic enantioselective amination reaction of 2-oxindoles catalyzed by biscinchona alkaloid catalysts [8]. Zhou [9][10] and Barbas [11][12], have independently reported similar
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Published 15 Apr 2016

The aminoindanol core as a key scaffold in bifunctional organocatalysts

  • Isaac G. Sonsona,
  • Eugenia Marqués-López and
  • Raquel P. Herrera

Beilstein J. Org. Chem. 2016, 12, 505–523, doi:10.3762/bjoc.12.50

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  • trifluoroethylamine moiety [3][4][5]. However, it is in the field of asymmetric organocatalysis [6][7][8] where the aminoindanol core has gained more importance, being a recurrent structural motif in several organocatalytic species. Some examples are (a) the enantioselective reduction of ketones through the in situ
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Published 14 Mar 2016
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