Synthesis of 2‐Phenyl‐ and 2,2‐Diarylpyrrolidines through Stevens Rearrangement Performed on Azetidinium Ions

Drouillat, Bruno; d'Aboville, Edouard; Bourdreux, Flavien; Couty, François

doi:10.1002/ejoc.201301536

Cited by 24 publications

(13 citation statements)

References 33 publications

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“…They unambiguously showed that it involves the formation of the ylide, which is the rate determining step, followed by the concerted rearrangement of the ylide involving a diradical intermediate stabilized within a solvent cage, and the migration with retention of configuration [140]. We also contributed to the knowledge of this reaction, demonstrating its regio-and diastereoselectivity [141][142][143]. Several examples are depicted in Scheme 79.…”

Section: Expansions Into Pyrroles Pyrrolidin-2-ones and Pyrrolidinesmentioning

confidence: 88%

“…Stevens rearrangement occurs exclusively, with total retention of the migrating carbon (C-3 of the pyrrolidine 321) and high regioselectivity. The second example outlines an efficient entry to 2,2-diarylpyrrolidines 323 recently published [143] based on this reaction with azetidinium such as 322, and the third one outlines the high chemoselectivity that can be reached, since only the primary benzylic (versus secondary) position of the azetidinium ion 324 is deprotonated here.…”

Section: Expansions Into Pyrroles Pyrrolidin-2-ones and Pyrrolidinesmentioning

confidence: 97%

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Ring Expansions of Nonactivated Aziridines and Azetidines

Couty

David

2015

Topics in Heterocyclic Chemistry

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Ring expansions promoted by ring strain in aziridines and azetidines are reviewed in this chapter, putting emphasis on recent applications from the last decade. This vast subject cannot be surveyed here exhaustively, and the reader will be guided to relevant precedent reviews or key reports. Rather, special attention will be put on selected examples and their mechanistic details, aiming to demonstrate that high selectivity can be reached in these reactions. In this issue, this fastgrowing topic has been divided into two distinct chapters, this one dealing with "nonactivated" aziridines and azetidines. Therefore, the reader will only find here examples involving NH-or N-alkylaziridines and N-azetidines as substrates for ring expansions, while N-acyl, N-carbamoyl, or N-tosyl compounds, defined as "activated" substrates, will be presented in the next chapter. This distinction can appear quite arbitrary at first sight but is amply justified by the great difference in reactivity of these distinct substrates. The first part focuses on the ring expansions of nonactivated aziridines into up to seven-membered rings and is further divided into expansions involving the incorporation of one (or more) heteroatoms, followed by ring expansions involving only incorporation of carbon atoms. The same model is then followed for azetidines.

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Section: Expansions Into Pyrroles Pyrrolidin-2-ones and Pyrrolidinesmentioning

confidence: 88%

Section: Expansions Into Pyrroles Pyrrolidin-2-ones and Pyrrolidinesmentioning

confidence: 97%

Ring Expansions of Nonactivated Aziridines and Azetidines

Couty

David

2015

Topics in Heterocyclic Chemistry

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“…The authors were also able to synthesize 2,2-diaryl-pyrrolidines 91 via azetidinium ylides 90 (Scheme 29). [23] Scheme 29. Stevens rearrangement of azetidinium ylides by Couty's group.…”

Section: Eurjocmentioning

confidence: 99%

Azetidiniums: Ring‐Expansion to Pyrrolidines, Piperidines, Azepanes, and Azocanes

2020

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“…For both the allylation system shown in Scheme A and the arylation system shown in Scheme B, electron‐withdrawing substituents at the 2‐position of the azetidinium ion are required for the observed [2,3]‐rearrangement. In contrast, analogous alkyl‐substituted derivatives were shown to undergo ring‐expansion processes through Stevens rearrangements …”

Section: Azetidine Functionalizationmentioning

confidence: 99%

Divergent Functionalizations of Azetidines and Unsaturated Azetidines

Reidl

Anderson

2019

Asian J Org Chem

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Azetidines are unusual heterocyclic motifs that comprise key components of biologically active molecules and provide desirable structural properties for drug discovery. While a variety of methods have been designed for the synthesis of azetidines, screening and optimization studies often require systematic and versatile strategies for varying structural characteristics. With this need in mind, this review surveys methods for the divergent preparation of substituted azetidines from starting materials that contain a 4-membered azacycle. The scope and tolerance of azetidine functionalization reactions are described including approaches such as lithiation and electrophilic trapping, nucleophilic displacement, and transition metal catalysis. To complement this discussion, opportunities for using unsaturated azetidines as precursors to functionalized saturated analogues are also examined as an emerging alternative tactic towards the diversity-oriented preparation of these strained heterocycles. The aim of this Minireview is to identify recent advances, as well as areas where further development is needed, to continue to inspire innovative solutions to the divergent synthesis of functionalized azetidines.[a] T.

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Synthesis of 2‐Phenyl‐ and 2,2‐Diarylpyrrolidines through Stevens Rearrangement Performed on Azetidinium Ions

Cited by 24 publications

References 33 publications

Ring Expansions of Nonactivated Aziridines and Azetidines

Ring Expansions of Nonactivated Aziridines and Azetidines

Azetidiniums: Ring‐Expansion to Pyrrolidines, Piperidines, Azepanes, and Azocanes

Divergent Functionalizations of Azetidines and Unsaturated Azetidines

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