Lewis acid promoted intramolecular (3 + 2) ‘cycloadditions’ of methyleneaziridines with alkene and alkyne acceptors

Griffin, Karen; Montagne, Cyril; Hoang, Cam Thuy; Clarkson, Guy J.; Shipman, Michael

doi:10.1039/c1ob06578e

Cited by 21 publications

(14 citation statements)

References 34 publications

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“…In 2004, they reported an efficient approach to access seven membered polycyclic systems via the Lewis acids promoted [ 149, respectively (Scheme 42). 62 In addition, the intermediate iminium ions, such as 150, could also be captured by cyanide to generate heterocycles 151 containing fully substituted stereocentres.…”

Section: Cycloadditionsmentioning

confidence: 99%

Synthesis and applications of methyleneaziridines

Pan

Zhao

2020

RSC Adv.

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Section: Cycloadditionsmentioning

confidence: 99%

Synthesis and applications of methyleneaziridines

Pan

Zhao

2020

RSC Adv.

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“…[19] The intramolecular BF 3 ·OEt 2 -mediated reactions led to the formation of cis-octahydrocyclopenta[c]pyrroles (e.g., 62 and 63, Scheme 13) and 2,4,5,6-tetrahydrocyclopenta[c]pyrroles (e.g., 67) through reactions with tethered alkenes and alkynes, respectively. [19] The intramolecular BF 3 ·OEt 2 -mediated reactions led to the formation of cis-octahydrocyclopenta[c]pyrroles (e.g., 62 and 63, Scheme 13) and 2,4,5,6-tetrahydrocyclopenta[c]pyrroles (e.g., 67) through reactions with tethered alkenes and alkynes, respectively.…”

Section: Reactions With Alkenes and Alkynes As Dipolarophilesmentioning

confidence: 99%

Aziridines in Formal [3+2] Cycloadditions: Synthesis of Five‐Membered Heterocycles

2012

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Chemistry based on ring opening of aziridines has been widely studied in organic synthesis. However, it has mainly been centered on ring opening by nucleophiles and on cycloaddition of azomethine ylides generated by carbon–carbon bond cleavage. In recent years, significant effort has been dedicated to study of the participation of aziridines in formal [3+2] cycloadditions, which provide routes for the construction of a wide variety of functionalized five‐membered heterocycles. Here we review the most relevant aspects of the reactivities and selectivities of aziridines as masked zwitterionic 1,3‐dipoles generated through C–N bond cleavage.

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“…Furthermore, Shipman and co-workers reported in 2012 the first example of intramolecular formal cycloaddition of methylene aziridines with alkenes. [188] Scheme 7.29: The use of diester-and vinyl-substituted aziridines in formal cycloaddition reactions.…”

Section: Formal [3+1] Cycloadditionsmentioning

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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Lewis acid promoted intramolecular (3 + 2) ‘cycloadditions’ of methyleneaziridines with alkene and alkyne acceptors

Cited by 21 publications

References 34 publications

Synthesis and applications of methyleneaziridines

Synthesis and applications of methyleneaziridines

Aziridines in Formal [3+2] Cycloadditions: Synthesis of Five‐Membered Heterocycles

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

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