Iron<sup>III</sup>-catalyzed asymmetric inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with simple olefins

Zhan, Tangyu; Zhou, Liang; Zhou, Yuqiao; Yang, Bingqian; Feng, Xiaoming; Liu, Xiaohua

doi:10.1039/d4sc00078a

Chem. Sci.

2024

DOI: 10.1039/d4sc00078a

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Iron^III-catalyzed asymmetric inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with simple olefins

Tangyu Zhan,

Liang Zhou,

Yuqiao Zhou

et al.

Abstract: A highly enantioselective [4 + 2] cycloaddition of a number of simple olefins with cyclic hetero-diene of dioxopyrrolidines is realized by a chiral iron(iii)/N,N′-dioxide complex catalyst.

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Cited by 8 publications

References 85 publications

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Formal High‐Order Cycloadditions of Donor‐Acceptor Cyclopropanes with Cycloheptatrienes

Borisov,

Platonov,

Sokolov

et al. 2024

Angewandte Chemie

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Design of various cycloaddition / annulation processes is one of the most intriguing challenges during all time in the development of the donor‐acceptor (D–A) cyclopropanes chemistry. In this work, a new missing class of formal high‐order [6+n]‐cycloaddition and annulation processes of D–A cyclopropanes with cycloheptatriene systems has been designed and reported, to fill a significant gap in the chemistry of D–A cyclopropanes. The reactivity of methylated cycloheptatrienes from Me1 to Me5 as well as unsubstituted cycloheptatriene was study in detail under GaCl3 activation conditions, which makes it possible to efficiently generate gallium 1,2‐zwitterionic complexes or 1,3‐zwitterionic intermediates from starting D–A cyclopropanes, when other Lewis acids are ineffective and non‐selective. New important examples of formal [6+2]‐, [6+3]‐, [6+4]‐, [6+1]‐, and [4+2]‐ cycloaddition and annulation reactions with cycloheptatrienes along with more complex processes were discovered. Cycloheptatriene itself also can successfully act as a hydride anion donor which allows ionic hydrogenation of D–A cyclopropanes to be performed under mild conditions. As a result, a number of efficient and highly diastereoselective protocols for the synthesis of seven‐membered‐based carbocycles has been developed.

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Formal High‐Order Cycloadditions of Donor‐Acceptor Cyclopropanes with Cycloheptatrienes

Borisov,

Platonov,

Sokolov

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Formal High‐Order Cycloadditions of Donor‐Acceptor Cyclopropanes with Cycloheptatrienes

Borisov,

Platonov,

Sokolov

et al. 2024

Angew Chem Int Ed

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Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway

Vazquez,

Spanevello,

Sarotti

et al. 2024

Eur J Org Chem

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Diels‐Alder between nitroalkenes derived from a sugar scaffold and cyclopentadiene were examined. Depending on chemical structure of nitroalkene and polarity of solvent used, the reaction proceeded via the formation of a nitronate intermediate. Cyclic nitronates highly functionalized were obtained as chemically stable and stereochemically pure compounds. [3,3] sigmatropic shift of these ones afforded the Diels Alder cycloadducts in quantitative yield. Mechanistic aspects of reaction between nitroalkenes and cyclopentadiene has been studied using DFT computational methods. Nitronate derivatives are attractive intermediates and open the way for the construction of valuable compounds with potential applications.

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Iron^III-catalyzed asymmetric inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with simple olefins

Abstract: A highly enantioselective [4 + 2] cycloaddition of a number of simple olefins with cyclic hetero-diene of dioxopyrrolidines is realized by a chiral iron(iii)/N,N′-dioxide complex catalyst.

Cited by 8 publications

References 85 publications

Formal High‐Order Cycloadditions of Donor‐Acceptor Cyclopropanes with Cycloheptatrienes

Formal High‐Order Cycloadditions of Donor‐Acceptor Cyclopropanes with Cycloheptatrienes

Formal High‐Order Cycloadditions of Donor‐Acceptor Cyclopropanes with Cycloheptatrienes

Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway

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IronIII-catalyzed asymmetric inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with simple olefins

Abstract: A highly enantioselective [4 + 2] cycloaddition of a number of simple olefins with cyclic hetero-diene of dioxopyrrolidines is realized by a chiral iron(iii)/N,N′-dioxide complex catalyst.

Cited by 8 publications

References 85 publications

Formal High‐Order Cycloadditions of Donor‐Acceptor Cyclopropanes with Cycloheptatrienes

Formal High‐Order Cycloadditions of Donor‐Acceptor Cyclopropanes with Cycloheptatrienes

Formal High‐Order Cycloadditions of Donor‐Acceptor Cyclopropanes with Cycloheptatrienes

Cyclic Nitronates via Sugar‐Derived Nitroalkenes in a Hetero‐Diels‐Alder/[3,3]‐Sigmatropic Rearrangement Pathway

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Product

Resources

About

Iron^III-catalyzed asymmetric inverse-electron-demand hetero-Diels–Alder reaction of dioxopyrrolidines with simple olefins