Cycloadditions of Aromatic Azomethine Imines with 1,1-Cyclopropane Diesters

Perreault, Christian; Goudreau, Sébastien R.; Zimmer, Lucie E.; Charette, André B.

doi:10.1021/ol702414e

Cited by 207 publications

(80 citation statements)

References 37 publications

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“…A nonconcerted mechanism combining nucleophilic ringopening of cyclopropane with subsequent nucleophilic addition was proposed. [82] The in situ generation of Niminoisoquinolinium ylide 30 derived from 2-alkynylbenzaldehyde hydrazide 15 was also employed in the [3+3] cycloaddition of cyclopropane diester. [83] As described in Scheme 34, a highly enantioselective [3+3] cycloaddition of the prepared aromatic Niminoisoquinolinium ylide 202 with cyclopropane diester 199 was achieved in the presence of a nickel catalyst.…”

Section: A C H T U N G T R E N N U N G [3+2] Cyclization Of N-imide Ymentioning

confidence: 99%

N‐Imide Ylide‐Based Reactions: CH Functionalization, Nucleophilic Addition and Cycloaddition

Qiu

Kuang

2014

Adv Synth Catal

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As valuable building blocks for introducing nitrogen, N-imide ylides represent an important class of reactive species and are synthons for the synthesis of nitrogen-containing heterocycles that potentially have biological activities. During the past decades, tremendous efforts have been devoted to the tandem processes involving N-imide ylides as well as their asymmetric applications. In particular, several types of N-imide ylide-based reactions have been established, such as C À H functionalization, nucleophilic addition, and cycloaddition, etc. In this review, recent advances in N-imide ylides chemistry are presented ordered according to the sequence of various reaction types.

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Section: A C H T U N G T R E N N U N G [3+2] Cyclization Of N-imide Ymentioning

confidence: 99%

N‐Imide Ylide‐Based Reactions: CH Functionalization, Nucleophilic Addition and Cycloaddition

Qiu

Kuang

2014

Adv Synth Catal

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“…In 2008, Charette and co-workers further demonstrated that the [3+3] cycloaddition between azomethine imines and donor-acceptor cyclopropanes was also possible (Equation 7.5). [105] In 2013, Tang and co-workers developed a highly enantioselective variation of this reaction using a C1-symmetric modified BOX ligand on the nickel. [106] Wu and co-workers developed domino-reactions in which the nitrone [107] or the azomethine imine [108] are generated in situ by addition of a nucleophile on a triple bond (Scheme 7.16, A and B).…”

Section: Formal [3+2] Cycloadditions With Cumulenesmentioning

confidence: 99%

Synthesis of Saturated Heterocycles via Metal-Catalyzed Formal Cycloaddition Reactions That Generate a C–N or C–O Bond

Waser

2013

Topics in Heterocyclic Chemistry

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In this section, the synthesis of saturated N-and O-heterocycles via formal cycloaddition is presented. The main focus is on metal-catalyzed reactions involving C-C or C-X  bond cleavage in three-or four-membered rings. After a fast presentation of pioneering works, the important breakthroughs of the last two decades are presented. The section starts with reactions involving three-membered rings. Formal [3+2] cycloadditions of donor-acceptor-substituted cyclopropanes and methylenecyclopropanes with carbonyls and imines are important methods to access tetrahydrofuran and pyrrolidine heterocycles. Formal [3+3] cycloadditions have emerged more recently. On the other hand, reactions of epoxides and aziridines with carbon monoxide or cumulenes are now well-established method to access heterocycles. These processes have been completed more recently with cycloaddition with olefins, carbonyls and imines. The section ends with the emerging field of four-membered ring activation for cycloaddition with  systems. This is the peer reviewed version of the following article: Top. Heterocycl. Chem. 2013, 32, 225, which The discovery of classical cycloaddition reactions, such as the (hetero) DielsAlder and 1,3-dipolar cycloadditions, has contributed tremendously to a more efficient access towards both carbocycles and heterocycles. The introduction of the term cycloaddition was necessary to distinguish these new types of reactions from previously discovered processes leading to cyclic structures, such as the famous Robinson annulation. In principle, each cycloaddition can be considered as a special case of the more general annulation process, but from which point on an annulation can be called a cycloaddition has been the topic of intensive discussions for decades, and is still not settled today. In 1968, Huisgen proposed a set of rules for the definition of cycloaddition, and the two first are still largely recognized as prerequisite: Although the rule that all the atoms of the starting materials have to be included in the product is not explicitly included in the definition, this requirement is usually recognized by most organic chemists. Even if electrocyclic cyclization processes were included in the original definition of Huisgen, the term cycloaddition is mostly used today for those reactions proceeding via the formation of at least two new bonds. Nevertheless, several researchers think that the term cycloaddition should be more strictly limited to reactions involving a continuous overlap of  electrons, and consequently allowing a concerted process. In fact, in his seminal publication, Huisgen already introduced further rules, in particular rule number 3, which explicitly stated that cycloadditions should not involve the cleavage of sigma bonds: -Huisgen Rule 3: "Cycloadditions do not involve the cleavage of  bonds." Unfortunately, in the same publication, Huisgen also described several reactions proceeding via -bond cleavage as cycloaddition. To solve this definition dilemma, several researchers have used th...

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“…However, usually it is impossible to isolate the corresponding intermediates that readily form the resulting heterocycles. These reactions, which have been reported in a large series of papers [formal (3+2)-cycloadditions to imines, [32][33][34][35] diazenes, [36][37][38][39] N-aryls, [40][41][42] heterocumulenes, [43][44][45] nitriles, [46][47][48][49][50][51][52][53] as well as (3+3)-cycloadditions [54][55][56][57] ], form an independent branch in DA cyclopropane chemistry that is considered to be beyond the scope of this review.…”

Section: Introductionmentioning

confidence: 99%

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles

et al. 2017

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Ring opening of donor-acceptor cyclopropanes with variousN-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor-acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitriles, and the azide ion are summarized.

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Cycloadditions of Aromatic Azomethine Imines with 1,1-Cyclopropane Diesters

Cited by 207 publications

References 37 publications

N‐Imide Ylide‐Based Reactions: CH Functionalization, Nucleophilic Addition and Cycloaddition

N‐Imide Ylide‐Based Reactions: CH Functionalization, Nucleophilic Addition and Cycloaddition

Synthesis of Saturated Heterocycles via Metal-Catalyzed Formal Cycloaddition Reactions That Generate a C–N or C–O Bond

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles

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Cycloadditions of Aromatic Azomethine Imines with 1,1-Cyclopropane Diesters

Cited by 207 publications

References 37 publications

N‐Imide Ylide‐Based Reactions: CH Functionalization, Nucleophilic Addition and Cycloaddition

N‐Imide Ylide‐Based Reactions: CH Functionalization, Nucleophilic Addition and Cycloaddition

Synthesis of Saturated Heterocycles via Metal-Catalyzed Formal Cycloaddition Reactions That Generate a C–N or C–O Bond

Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleo­philes

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Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles