Chiral Fidelity in the Diastereoselective and Enantiospecific Synthesis of Indenes from Axially Chiral Benzylidene Cyclanes

Mouysset, Dominique; Tessonnier, Cyril; Tintaru, Aura; Dumur, Frédéric; Jean, Marion; Vanthuyne, Nicolas; Bertrand, M.; Siri, Didier; Nechab, Malek

doi:10.1002/chem.201701501

Cited by 5 publications

(2 citation statements)

References 39 publications

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“…Nechab′s group proposed a new pathway to build the indene 124 scaffold through diastereo‐ and enantioselective cyclizations using original axially chiral benzylidene cyclanes 121 . This cascade process involved copper‐catalyzed homologation of the terminal alkyne, in situ base‐catalyzed allenoate 123 formation and Alder‐ene cyclization (Scheme ).…”

Section: Transition Metal (Tm)‐catalyzed Processesmentioning

confidence: 99%

Recent Advances in the Synthesis of Indenes

2019

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Indenes constitute an important class of molecules which continue to attract interest from the synthetic organic chemists′ community because not only many natural and synthetic compounds embodying the indene skeleton display bioactivity or pharmaceutical activity but also because indenes find applications in material science, e.g. in photovoltaic solar cells and in the preparation of new fluorescent materials, and in the preparation of metal complexes with special catalytic activity. Many approaches have been exploited in the last four years to build this bicyclic system, the two most explored being cationic processes involving an intramolecular Friedel‐Crafts reaction and those in which a transition metal plays a key role in assembling the indene framework. In this review the results of the synthetic efforts toward indenes made in the 2016–2019 period are reviewed.

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Section: Transition Metal (Tm)‐catalyzed Processesmentioning

confidence: 99%

Recent Advances in the Synthesis of Indenes

2019

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“…Instead, concomitant studies making use of chiral cycloalkylidenes to control chirality transfer in the same type of cascading rearrangement proved to be successful. 25…”

Section: Transfer Of Chiralitymentioning

confidence: 99%

Organocopper triggered cyclization of conjugated dienynesviatandem S_N2′/Alder-ene reaction

et al. 2018

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Palladium‐Catalyzed Intramolecular Alder‐Ene Type Cycloisomerization Reactions

Yadav

Ramasastry

2020

Chemistry An Asian Journal

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An overview of the recent literature on palladium‐catalyzed intramolecular Alder‐ene (IMAE) reaction of a variety of 1,n‐unsaturated systems is presented. The reaction which was first reported by Trost and Lautens provided an efficient alternative to the thermal or Lewis acid catalyzed cycloisomerizations involving ene‐type reaction. The IMAE cyclization of enynes and dienes has emerged as an important area and found significant applications in building up of complex molecular architectures and in the synthesis of several bioactive natural products. Since highly impactful reviews on this subject have covered the literature till 2015, this article focuses on summarizing the works subsequent to 2015.

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Chiral Fidelity in the Diastereoselective and Enantiospecific Synthesis of Indenes from Axially Chiral Benzylidene Cyclanes

Cited by 5 publications

References 39 publications

Recent Advances in the Synthesis of Indenes

Recent Advances in the Synthesis of Indenes

Organocopper triggered cyclization of conjugated dienynesviatandem S_N2′/Alder-ene reaction

Palladium‐Catalyzed Intramolecular Alder‐Ene Type Cycloisomerization Reactions

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Chiral Fidelity in the Diastereoselective and Enantiospecific Synthesis of Indenes from Axially Chiral Benzylidene Cyclanes

Cited by 5 publications

References 39 publications

Recent Advances in the Synthesis of Indenes

Recent Advances in the Synthesis of Indenes

Organocopper triggered cyclization of conjugated dienynesviatandem SN2′/Alder-ene reaction

Palladium‐Catalyzed Intramolecular Alder‐Ene Type Cycloisomerization Reactions

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Organocopper triggered cyclization of conjugated dienynesviatandem S_N2′/Alder-ene reaction