Access to novel functionalized trifluoromethyl β-lactams by ring expansion of aziridines

Decamps, Sophie; Sevaille, Laurent; Ongeri, Sandrine; Crousse, Benoı̂t

doi:10.1039/c4ob01262c

Cited by 24 publications

(11 citation statements)

References 21 publications

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“…The addition occurred exclusively from the opposite side of the bulky trifluoromethyl substituent. This result has already been observed during our reactions of Li/Br exchange from 3-Br 4-CF 3 lactams and aldehydes (Decamps et al, 2014).…”

Section: Resultssupporting

confidence: 85%

“…Although fluorine-containing compounds have been widely used in the field of medicinal chemistry (Wang et al, 2014; Zhu et al, 2014; Zhou et al, 2016) due to their pharmacological properties, 4-CF 3 monobactams functionalized at C-3 are slightly exploited. The synthesis of 4-CF 3 monosubstituted β-lactams at the C-3 position are reported and prepared according to different ways: Staudinger reaction (Guanti et al, 1985; Abouabdellah et al, 1997; Petrik et al, 2011), ring expansion of aziridines via halogen-metal exchange (Decamps et al, 2014), Kinugasa reaction (Kowalski et al, 2016), and the Reformatsky reaction (Trulli et al, 2018). The alkylation reaction with non-fluorinated β-lactams using lithium amide, such as LDA and Li/KHDMS, to obtain the alkylated products at C-3 was well documented in the literature (Kuhlein and Jensen, 1974; Kamath and Ojima, 2012; Deketelaere et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

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Direct Access to Substituted 4-CF3 β-Lactams at the C-3 Position

et al. 2019

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Section: Resultssupporting

confidence: 85%

Section: Introductionmentioning

confidence: 99%

Direct Access to Substituted 4-CF3 β-Lactams at the C-3 Position

et al. 2019

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“…The same type of rearrangement (Scheme 17) can be applied to the preparation of azetidinones from aziridine carboxylates as shown by Clough in 1974 [54] and reinvestigated more than 30 years later by Sharma [55] and very recently optimized by Crousse with trifluoro-substituted aziridines [56].…”

Section: Expansion Into Azetidines and Azetidinonesmentioning

confidence: 92%

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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“…[109] Furthermore,a na mine equivalent has been introduced at C3 by reaction of 3-bromoazetidin-2-one 132,g enerated by ring expansion of the corresponding aziridine, with di-tert-butylazodicarboxylate (DBAD)a fter lithium-halogen exchange, resulting in b-lactam 133 (Scheme 30). [110]…”

Section: -Halo-b-lactamsmentioning

confidence: 99%

Synthetic Approaches toward Monocyclic 3‐Amino‐β‐lactams

et al. 2017

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Due to the emerging resistance against classical β‐lactam‐based antibiotics, a growing number of bacterial infections has become harder to treat. This alarming tendency necessitates continued research on novel antibacterial agents. Many classes of β‐lactam antibiotics are characterized by the presence of the 3‐aminoazetidin‐2‐one core, which resembles the natural substrate of the target penicillin‐binding proteins. In that respect, this Review summarizes the different synthetic pathways toward this key structure for the development of new antibacterial agents. The most extensively applied methods for 3‐amino‐β‐lactam ring formation are discussed, in addition to a few less common strategies. Moreover, approaches to introduce the 3‐amino substituent after ring formation are also covered.

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Access to novel functionalized trifluoromethyl β-lactams by ring expansion of aziridines

Abstract: From carboxylic acid trifluoromethyl aziridines, halogeno β-lactams were obtained stereoselectively by ring expansion. Different conditions such as radical, organometallic reactions allowed easy and selective access to CF3-β-lactams substituted at the C-3 position.

Cited by 24 publications

References 21 publications

Direct Access to Substituted 4-CF3 β-Lactams at the C-3 Position

Direct Access to Substituted 4-CF3 β-Lactams at the C-3 Position

Ring Expansions of Nonactivated Aziridines and Azetidines

Synthetic Approaches toward Monocyclic 3‐Amino‐β‐lactams

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