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  1. Article ; Online: Enantioselective Strategies for The Synthesis of N-N Atropisomers.

    Centonze, Giovanni / Portolani, Chiara / Righi, Paolo / Bencivenni, Giorgio

    Angewandte Chemie (International ed. in English)

    2023  Volume 62, Issue 31, Page(s) e202303966

    Abstract: Axially chiral compounds have been always considered a laboratory curiosity with rare prospects of being applied in asymmetric synthesis. Things have changed very quickly in the last twenty years when it was understood the important role and the enormous ...

    Abstract Axially chiral compounds have been always considered a laboratory curiosity with rare prospects of being applied in asymmetric synthesis. Things have changed very quickly in the last twenty years when it was understood the important role and the enormous impact that these compounds have in medicinal, biological and material chemistry. The asymmetric synthesis of atropisomers became a rapidly expanding field and recent reports on the development of N-N atropisomers strongly prove how this research field is a hot topic open to new challenges and frontiers of asymmetric synthesis. This review focuses on the recent advances in the enantioselective synthesis of N-N atropisomers highlighting the strategies and breakthroughs to obtain this novel and stimulating atropisomeric framework.
    Language English
    Publishing date 2023-05-15
    Publishing country Germany
    Document type Journal Article ; Review
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202303966
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Computational Investigation on the Origin of Atroposelectivity for the Cinchona Alkaloid Primary Amine-Catalyzed Vinylogous Desymmetrization of

    Tampellini, Nicolò / Righi, Paolo / Bencivenni, Giorgio

    The Journal of organic chemistry

    2021  Volume 86, Issue 17, Page(s) 11782–11793

    Abstract: Mechanistic studies clarifying how chiral primary amines control the stereochemistry of vinylogous processes are rare. We report a density functional theory (DFT) computational study for the comprehension of the reaction mechanism of the vinylogous ... ...

    Abstract Mechanistic studies clarifying how chiral primary amines control the stereochemistry of vinylogous processes are rare. We report a density functional theory (DFT) computational study for the comprehension of the reaction mechanism of the vinylogous atroposelective desymmetrization of
    MeSH term(s) Amines ; Catalysis ; Cinchona Alkaloids ; Maleimides ; Stereoisomerism
    Chemical Substances Amines ; Cinchona Alkaloids ; Maleimides
    Language English
    Publishing date 2021-08-04
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.1c01235
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article: Organocatalytic Strategies for the Synthesis of Axially Chiral Compounds

    Bencivenni, Giorgio

    Synlett

    2015  Volume 26, Issue 14, Page(s) 1915–1922

    Abstract: Atropisomers are compounds in which chirality arises from hindered rotation along the carbon–carbon or carbon–heteroatom single bond. Recently, organocatalysis appeared to be a rapid, valuable, and efficient strategy for their preparation in an ... ...

    Abstract Atropisomers are compounds in which chirality arises from hindered rotation along the carbon–carbon or carbon–heteroatom single bond. Recently, organocatalysis appeared to be a rapid, valuable, and efficient strategy for their preparation in an enantioselective manner. In this report a general overview of the most important organocatalyzed atroposelective transformations will be given pointing out in particular the specific role played by the catalyst. 1

    Dynamic Kinetic Resolution 2

    Desymmetrization of Biaryls 3

    Direct Synthesis of Biaryls 4

    Asymmetric Friedel–Crafts Amination of Naphthols 5

    N-Alkylation via Phase-Transfer Catalysis 6

    Desymmetrization of N -Arylmaleimides
    Keywords atropisomers ; organocatalysis ; enantioselective synthesis ; desymmetrization ; dynamic kinetic resolution
    Language English
    Publishing date 2015-06-24
    Publisher © Georg Thieme Verlag
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2042012-2
    ISSN 1437-2096 ; 0936-5214
    ISSN (online) 1437-2096
    ISSN 0936-5214
    DOI 10.1055/s-0034-1378712
    Database Thieme publisher's database

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  4. Article ; Online: Organocatalytic Desymmetrization Reactions for the Synthesis of Axially Chiral Compounds.

    Di Iorio, Nicola / Crotti, Simone / Bencivenni, Giorgio

    Chemical record (New York, N.Y.)

    2019  Volume 19, Issue 10, Page(s) 2095–2104

    Abstract: The enantioselective synthesis of atropisomers is an emerging field, that in recent years reached fundamental results and put the bases for innovative applications. Organocatalysis is playing a central role in the realization of original synthesis for ... ...

    Abstract The enantioselective synthesis of atropisomers is an emerging field, that in recent years reached fundamental results and put the bases for innovative applications. Organocatalysis is playing a central role in the realization of original synthesis for novel atropisomeric scaffolds.
    Language English
    Publishing date 2019-02-07
    Publishing country United States
    Document type Journal Article ; Review
    ZDB-ID 2044646-9
    ISSN 1528-0691 ; 1527-8999
    ISSN (online) 1528-0691
    ISSN 1527-8999
    DOI 10.1002/tcr.201800194
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Giuseppe Bartoli (1941-2020).

    Dalpozzo, Renato / Bencivenni, Giorgio / Sambri, Letizia / Marcantoni, Enrico / Melchiorre, Paolo

    Angewandte Chemie (International ed. in English)

    2020  Volume 59, Issue 18, Page(s) 6962

    Language English
    Publishing date 2020-03-13
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202002941
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: Synthesis of Atropisomeric Hydrazides by One-Pot Sequential Enantio- and Diastereoselective Catalysis.

    Portolani, Chiara / Centonze, Giovanni / Luciani, Sara / Pellegrini, Andrea / Righi, Paolo / Mazzanti, Andrea / Ciogli, Alessia / Sorato, Andrea / Bencivenni, Giorgio

    Angewandte Chemie (International ed. in English)

    2022  Volume 61, Issue 42, Page(s) e202209895

    Abstract: The first catalytic enantioselective and diastereoselective synthesis of atropisomeric hydrazides was achieved using a sequential catalysis protocol. This strategy is based on a one-pot sequence of two organocatalytic cycles featuring the enamine ... ...

    Abstract The first catalytic enantioselective and diastereoselective synthesis of atropisomeric hydrazides was achieved using a sequential catalysis protocol. This strategy is based on a one-pot sequence of two organocatalytic cycles featuring the enamine amination of branched aldehydes followed by nitrogen alkylation under phase-transfer conditions. The resulting axially chiral hydrazides were obtained directly from commercially available reagents in high yields and with good stereocontrol. The permutation of organocatalysts allowed easy access to all stereoisomers, enabling a stereodivergent approach to enantioenriched atropisomeric hydrazides.
    MeSH term(s) Aldehydes ; Amination ; Catalysis ; Hydrazines ; Molecular Structure ; Nitrogen ; Stereoisomerism
    Chemical Substances Aldehydes ; Hydrazines ; Nitrogen (N762921K75)
    Language English
    Publishing date 2022-09-12
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202209895
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: On the Nature of the Rotational Energy Barrier of Atropisomeric Hydrazides.

    Pellegrini, Andrea / Marcon, Laura / Righi, Paolo / Centonze, Giovanni / Portolani, Chiara / Capodiferro, Marco / Oljira, Shilashi Badasa / Manetto, Simone / Ciogli, Alessia / Bencivenni, Giorgio

    Molecules (Basel, Switzerland)

    2023  Volume 28, Issue 23

    Abstract: N-N atropisomers represent a useful class of compounds that has recently received important attention from many research groups. This article presents an in-depth analysis of the energy barrier needed for the racemization process of atropoisomeric ... ...

    Abstract N-N atropisomers represent a useful class of compounds that has recently received important attention from many research groups. This article presents an in-depth analysis of the energy barrier needed for the racemization process of atropoisomeric hydrazides, combining an experimental and computational approach. The focus is on examining how electronic and steric factors impact the racemization process. The results obtained indicate that the barrier observed during the racemization process mainly arises from an increase in the p-orbital character of the nitrogen atoms.
    Language English
    Publishing date 2023-11-29
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 1413402-0
    ISSN 1420-3049 ; 1431-5165 ; 1420-3049
    ISSN (online) 1420-3049
    ISSN 1431-5165 ; 1420-3049
    DOI 10.3390/molecules28237856
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  8. Article ; Online: Direct Access to Alkylideneoxindoles via Axially Enantioselective Knoevenagel Condensation.

    Crotti, Simone / Di Iorio, Nicola / Artusi, Chiara / Mazzanti, Andrea / Righi, Paolo / Bencivenni, Giorgio

    Organic letters

    2019  Volume 21, Issue 9, Page(s) 3013–3017

    Abstract: The organocatalytic axially enantioselective Knoevenagel condensation between prochiral cyclohexanones and oxindoles is presented. The reaction, promoted by a primary amine, proceeded smoothly and furnished unprecedented examples of novel cyclohexylidene ...

    Abstract The organocatalytic axially enantioselective Knoevenagel condensation between prochiral cyclohexanones and oxindoles is presented. The reaction, promoted by a primary amine, proceeded smoothly and furnished unprecedented examples of novel cyclohexylidene oxindoles displaying axial chirality.
    Language English
    Publishing date 2019-04-12
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.9b00505
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  9. Article ; Online: First enantioselective synthesis of gingesulfonic acids and unequivocal determination of their absolute stereochemistry.

    Bencivenni, Grazia / Moccia, Maria / Ravelli, Andrea / Gillick-Healy, Malachi W / Kelly, Brian G / Adamo, Mauro F A

    Organic & biomolecular chemistry

    2020  Volume 18, Issue 6, Page(s) 1091–1094

    Abstract: Herein we report the first organocatalysed enantioselective synthesis of gingesulfonic acids and shogasulfonic acids via a mild and convenient aminothiourea-catalysed conjugate addition of bisulfite to the olefin moiety of α,β-unsaturated carbonyls-a ... ...

    Abstract Herein we report the first organocatalysed enantioselective synthesis of gingesulfonic acids and shogasulfonic acids via a mild and convenient aminothiourea-catalysed conjugate addition of bisulfite to the olefin moiety of α,β-unsaturated carbonyls-a technology previously reported by us. A series of optically active naturally occurring sulfonic acids are prepared in their natural and unnatural configurations, and their absolute configurations are unequivocally confirmed by single crystal X-ray diffractometry.
    Language English
    Publishing date 2020-01-29
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/c9ob02662b
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article ; Online: Enantioselective Synthesis of 3,4-Dihydropyran-2-ones via Phase-Transfer-Catalyzed Addition-Cyclization of Acetylacetone to Cinnamic Thioesters.

    Destro, Dario / Bottinelli, Carlo / Ferrari, Ludovica / Albanese, Domenico C M / Bencivenni, Grazia / Gillick-Healy, Malachi W / Kelly, Brian G / Adamo, Mauro F A

    The Journal of organic chemistry

    2020  Volume 85, Issue 8, Page(s) 5183–5192

    Abstract: Herein, we present the first example of synthesis of 3,4-dihydropyran-2-ones from cinnamic thioesters via a stereoselective phase-transfer-catalyzed domino Michael-cyclization reaction with acetylacetone. The reaction proceeded under the catalysis ... ...

    Abstract Herein, we present the first example of synthesis of 3,4-dihydropyran-2-ones from cinnamic thioesters via a stereoselective phase-transfer-catalyzed domino Michael-cyclization reaction with acetylacetone. The reaction proceeded under the catalysis of
    Language English
    Publishing date 2020-04-01
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.9b03216
    Database MEDical Literature Analysis and Retrieval System OnLINE

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