Phenylaziridine as a 1,3-dipole. Application to the synthesis of functionalized pyrrolidines

Ungureanu, Ioana; Bologa, Cristian; Chayer, Saïd; Mann, André

doi:10.1016/s0040-4039(99)01002-3

Cited by 47 publications

(22 citation statements)

References 20 publications

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“…This new use of 1 as a 1,3-dipole precursor is an advance on our recent work, [3] and of importance, not only from its theoretical, but also from its preparative significance in providing direct access to substituted pyrrolidines. This new use of 1 as a 1,3-dipole precursor is an advance on our recent work, [3] and of importance, not only from its theoretical, but also from its preparative significance in providing direct access to substituted pyrrolidines.…”

Section: In Memory Of Toshiro Ibukamentioning

confidence: 96%

Phenylaziridine as a Masked 1,3 Dipole in Reactions with Nonactivated Alkenes

Ungureanu¹,

Klotz²,

Mann³

2000

Angew. Chem. Int. Ed.

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Section: In Memory Of Toshiro Ibukamentioning

confidence: 96%

Phenylaziridine as a Masked 1,3 Dipole in Reactions with Nonactivated Alkenes

Ungureanu¹,

Klotz²,

Mann³

2000

Angew. Chem. Int. Ed.

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“…Bergmeier and co-workers demonstrated that the intramolecular cycloaddition of tosyl aziridines and allyl silanes could be catalyzed by boron-trifluoride etherate (Scheme 7.28, A). [180] Also in 1999, Mann and co-workers used the same catalyst for the intermolecular cycloaddition of arylsubstituted aziridines with enol ethers, [181] and later demonstrated that this system could also be applied to non-activated alkenes (Scheme 7.28, B). [182] In these early works, high diastereoselectivity could be achieved only in the case of the formation of bicyclic five-five ring systems.…”

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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“…[8][9][10][11] In contrast with classical 1,3-dipoles, which are internally stabilized by delocalization, the substitution pattern of 13 allows external stabilization by both the aromatic and the tosyl groups. [8][9][10][11] In contrast with classical 1,3-dipoles, which are internally stabilized by delocalization, the substitution pattern of 13 allows external stabilization by both the aromatic and the tosyl groups.…”

Section: Reactions With Alkenes and Alkynes As Dipolarophilesmentioning

confidence: 99%

“…pyran 14a or tetrahydropyridine 14b each resulted in the formation of only one regioisomer (15a or 15b, respectively) in good yield. [8][9][10][11][12] The synthesis of bicyclic proline analogues through intramolecular formal [3+2] cycloadditions involving aziridines and allylsilanes was reported by Bergmeir and coworkers. It was later demonstrated that the reaction between 12a and dihydropyran 14a could also be achieved with Cu(OTf) 2 catalysis, leading to a 2:3 mixture of exo and endo bicyclic pyrrolidine derivatives 15a, although the combined overall yield was lower (45 %).…”

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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Phenylaziridine as a 1,3-dipole. Application to the synthesis of functionalized pyrrolidines

Cited by 47 publications

References 20 publications

Phenylaziridine as a Masked 1,3 Dipole in Reactions with Nonactivated Alkenes

Phenylaziridine as a Masked 1,3 Dipole in Reactions with Nonactivated Alkenes

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

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

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