Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings

Otevrel, Jan; Eugui, Macarena; Ričko, Sebastijan; Jørgensen, Karl Anker

doi:10.1038/s44160-023-00416-1

Cited by 9 publications

(2 citation statements)

References 123 publications

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“…In consideration of widely-existing of chiral medium-sized rings in natural products and bioactive molecules 15–17 (Scheme 1C), the development of long-chained allene-derived biselectrophiles to construct medium-sized rings, especially enantioselectively, would be in high demand. Herein, we report a phosphine-catalyzed [6 + 1] annulation of α-allyl allenoates with 1,1-bisnucleophiles, achieving a general and economical approach for the synthesis of seven-membered rings (Scheme 1D) which is different with the previous works through [4 + 3] annulation.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective phosphine-catalyzed [6 + 1] annulations of α-allyl allenoates with 1,1-bisnucleophiles

Lai,

Cai,

Huang

2024

Chem. Sci.

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Section: Introductionmentioning

confidence: 99%

Enantioselective phosphine-catalyzed [6 + 1] annulations of α-allyl allenoates with 1,1-bisnucleophiles

Lai,

Cai,

Huang

2024

Chem. Sci.

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“…[6][7][8] Recently, cycloadditions involving more than 6π-electronshigher-order cycloadditions -have proven an efficient tool to generate chemical complexity in a single transformation. [9][10][11][12] The understanding and terminology of higher-order cycloadditions have mainly been presented on a case-by-case basis as each new system is investigated separately, leading to an ambiguous rhetoric for these reactions. In particular, cyclo-additions employing π-systems which involve heteroatoms have often been described by the number of atoms rather than electrons, which participate in the formation of the new cyclic system.…”

Section: Introductionmentioning

confidence: 99%

On the Number of π‐Electrons Involved in Stepwise Cycloaddition Reactions

Inunnguaq Jessen,

Izzo,

Modlinski

et al. 2023

Chemistry A European J

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The development of higher‐order cycloadditions has mainly been restricted by the requisite usage of highly conjugated and reactive π‐systems. Recent years have witnessed organocatalysis as a potent mediator for several of the challenges associated herein, rendering higher‐order cycloadditions a legitimate option for achieving the selective construction of specific molecular scaffolds. These developments reinvigorate the efforts to try to understand the underlying principles for cycloadditions involving a higher numbers of π‐electrons than the “classical” cycloadditions; how do we properly address the impact which the addition of further π‐electrons have on the reactivity of a system? Herein, computational investigations of two model higher‐order cycloaddition systems have been performed to try to provide insights on changes in energetic barriers induced by the presence of benzofusions in a position which is unobstructive to the reactivity. With experimental substantiation as support, these studies might open up for a discussion on whether the π‐electrons of benzofused systems simply act as spectator electrons, or play a tangible role on the observed reactivity to an extent, where a distinct nomenclature is meritable.

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Tropone Hydrazides in [10+2]‐Hetero‐Higher‐Order Cycloaddition for the Synthesis of Tetrahydropyridazine Derivatives

Cieśliński,

Przydacz,

Sieroń

et al. 2024

Adv Synth Catal

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[10+2]‐Hetero‐higher‐order cycloaddition between tropone hydrazides (acting as 10π‐components) and 3‐alkylidene oxindoles (acting as 2π‐components) has been established. Under Brønsted base catalysis the reaction proceeded in a fully peri‐ and diastereoselective manner with the stereochemical outcome governed mainly by electronic interactions. Following such a strategy, a series of structurally diverse tetrahydropyridazines were prepared in 30‐70% yields. Furthermore, the potential of the obtained cycloadducts has been confirmed in selected chemoselective transformations.

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Enantioselective organocatalytic cycloadditions for the synthesis of medium-sized rings

Cited by 9 publications

References 123 publications

Enantioselective phosphine-catalyzed [6 + 1] annulations of α-allyl allenoates with 1,1-bisnucleophiles

Enantioselective phosphine-catalyzed [6 + 1] annulations of α-allyl allenoates with 1,1-bisnucleophiles

On the Number of π‐Electrons Involved in Stepwise Cycloaddition Reactions

Tropone Hydrazides in [10+2]‐Hetero‐Higher‐Order Cycloaddition for the Synthesis of Tetrahydropyridazine Derivatives

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