Strained Aziridinium Ion

Ranjith, Jala; Ha, Hyun‐Joon

doi:10.1002/9781119757153.ch15

Cited by 2 publications

(6 citation statements)

References 58 publications

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“…Especially, we were able to get syn or antiproduct as we want in a stereoselective manner by leading different reaction conditions such as chelation and nonchelation pathway (Scheme 1). 6 …”

Section: Figurementioning

confidence: 99%

“…Once we obtained the diaryl product 7 , the aziridine ring as its starting material was able to be served as various amine functional groups by the nucleophilic ring openings with the assistance of protic or Lewis acid. Most nucleophilic reactions occurred at the less hindered C3 position of the 2‐substituted alkyl aziridine 6 …”

Section: Figurementioning

confidence: 99%

“…5 Especially, we were able to get syn or antiproduct as we want in a stereoselective manner by leading different reaction conditions such as chelation and nonchelation pathway (Scheme 1). 6 However, up to recently, we have not been able to further functionalization the resultant hydroxy aziridine (4a) until we observed the α-aziridinyl carbenium ion as an intermediate (4b or 4b 0 ) observed for the first time from the reaction of aziridin-2-yl arylmethanol 3 with Lewis acid BF 3 ÁOEt 2 (Scheme 2). 7…”

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confidence: 96%

“…Most nucleophilic reactions occurred at the less hindered C3 position of the 2-substituted alkyl aziridine. 6 To achieve the target 2,3,3-triarylpropylamine we tried several different reactions specifically for an application of the third aryl group at the β-position of the amine as in either 2-aminopropane or 1-aminopropane by the ringopening reaction. However, we were not able to get a detectable amount of arylated reaction product.…”

mentioning

confidence: 99%

“…During this study, we found an interesting transformation that the starting 1-(aziridine-2-yl)-arylmethanol 3 with either syn or antistereochemistry reacted with electron-rich phenolic second aryl group 11 to give rise to 3-(4-methoxyphenyl)-(2,3-dihydrobenzofuran-2-yl)methanamine (10). This product came from an intramolecular aziridine ring-opening reaction then the nucleophilic hydroxy group at the second aryl group T A B L E 1 Optimization of protic acid mediated synthesis of 2,3,3-tris (4-methoxyphenyl)-N-((R)-1-phenylethyl)propan-1-amine (1a) from chiral (S)-5-(bis(4-methoxyphenyl)methyl)-3-((R)-1-phenylethyl)oxazolidin-2-one (8a) as a model substrate and Anisole (6).…”

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confidence: 99%

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Synthesis of diverse aryl‐substituted amino propanes

Yoo,

Yi,

2024

Bulletin Korean Chem Soc

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Amines bearing diverse aryl substituents for potential utilities as energy and new materials have been synthesized from aziridine‐2‐carboxaldehyde and diverse aryl‐containing substrates. At first two aryl groups were to yield (aziridine‐2‐yl)‐1,1‐diaryl‐methane which was converted to 5‐diarylmethyl oxazolidin‐2‐one as a synthetic intermediate. They were further reacted with another aryl group in the presence of methanesulfonic acid to yield 2,3,3‐triarylpropylamine with the possible carbenium ion intermediate. In addition, this reaction with a second additional phenolic aryl group gave rise to the diversely substituted 3‐(4‐methoxyphenyl)‐(2,3‐dihydrobenzofuran‐2‐yl)methanamine derived from the intramolecular aziridine ring‐opening reaction by hydroxy group at phenol.

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Section: Figurementioning

confidence: 99%

Section: Figurementioning

confidence: 99%

mentioning

confidence: 96%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis of diverse aryl‐substituted amino propanes

Yoo,

Yi,

2024

Bulletin Korean Chem Soc

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Regioselective ring opening of aziridine for synthesizing azaheterocycle

Srivastava,

2023

Front. Chem.

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Aziridine had different regioselective ring openings depending on the functional group of its alkyl substituent. In the case of the alkyl group bearing γ-ketone at the C2 substituent of aziridine, the ring opening by the hydroxy nucleophile from H2O occurred by attacking the aziridine carbon at the C2 position. This reaction proceeded efficiently in the presence of CF3CO2H. Interestingly, the same starting aziridine ring bearing the alkyl substituent at the C2 position with the γ-silylated hydroxy group instead of γ-ketone led to the ring-opening reaction by the same oxygen nucleophile at the unsubstituted C3 position, with the breakage of the bond between aziridine N1 nitrogen and carbon at C3. These reaction products were cyclized to afford substituted pyrrolidine and piperidine rings with representative examples of congeners of pseudoconhydrine and monomorine.

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Strained Aziridinium Ion

Cited by 2 publications

References 58 publications

Synthesis of diverse aryl‐substituted amino propanes

Synthesis of diverse aryl‐substituted amino propanes

Regioselective ring opening of aziridine for synthesizing azaheterocycle

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