The Aza-Wharton Reaction: Syntheses of Cyclic Allylic Amines and Vicinal Hydroxyamines from the Respective Acylaziridines

Silva, Saúl; Rodrigues, Paula C.; Bento, Isabel; Maycock, Christopher D.

doi:10.1021/jo5029387

Cited by 10 publications

(2 citation statements)

References 18 publications

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“…Reaction time: 72 h; yield: 27.1 mg (28%); yellow oil; R f = 0.28 (95:5 hexane/EtOAc). -2-en-1-yl)-4-methoxyaniline (P11) 30 Reaction time: 72 h; yield: 25.4 mg (25%); yellow oil; R f = 0.27 (98:2 hexane/EtOAc). N-(1,3-Diphenylprop-2-yn-1-yl…”

Section: -Methoxy-n-(pentan-2-yl)aniline (P10) 28mentioning

confidence: 99%

Hydrogen-Borrowing Amination of Secondary Alcohols Promoted by a (Cyclopentadienone)iron Complex

et al. 2019

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Thanks to a highly active catalyst, the scope of the (cyclopentadienone)iron complex-promoted ‘hydrogen-borrowing’ (HB) amination has been expanded to secondary alcohols, which had previously been reported to react only in the presence of large amounts of co-catalysts. A range of cyclic and acyclic secondary alcohols were reacted with aromatic and aliphatic amines giving fair to excellent yields of the substitution products. The catalyst was also able to promote the cyclization of diols bearing a secondary alcohol group with primary amines to generate saturated N-heterocycles.

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Section: -Methoxy-n-(pentan-2-yl)aniline (P10) 28mentioning

confidence: 99%

Hydrogen-Borrowing Amination of Secondary Alcohols Promoted by a (Cyclopentadienone)iron Complex

et al. 2019

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“…The aza-Wharton reaction (an eliminative Wolff-Kishner reduction of an α-substituted ketone) of a range of cyclic 2acylaziridines 141 was studied and shown to be a viable method for the preparation of cyclic allylic amines and vicinal amino alcohols 143 (Scheme 31). 46 Three procedures were used to carry out the reaction; although it was much faster under acidic conditions, the yields in some cases were higher under basic ones. Target amines 143 were obtained stereoselectively and, in some cases, enantiomerically pure.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Recent Advances in the Chemistry of 2-Acylaziridines

Pankova

Кузнецов

2017

Synthesis

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This review highlights recent achievements in the transformations of 2-acylaziridines toward the synthesis of cyclic and acyclic nitrogen-containing compounds. The influence of a carbonyl group on reaction selectivity is discussed.1 Introduction2 Reactions via C–C Bond Cleavage3 Reactions via C–N Bond Cleavage3.1 Reactions Starting with the Aziridine Ring Opening3.2 Reactions Starting at the Carbonyl Group4 Conclusion

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Synthesis of Cyclohexenone(aryl)iodonium Salts and Their Application in Construction of Fused aza‐Heterocyclic Skeletons

Zhang,

Xu,

et al. 2024

Adv Synth Catal

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A class of cyclohexenone(aryl)iodonium salts was readily prepared from 2‐iodocyclohexenones and arenes under mild conditions. This novel series of hypervalent iodonium building blocks exhibits dual characteristics of hyperiodonium salts and α,β‐unsaturated cyclic ketones, enabling access to intricate aza‐heterocycles. The reaction of these cyclohexenone(aryl)iodonium salts with arylamines and benzene sulfonamides affords 2‐acylaziridines, while with 1H‐imidazol‐2‐amines leads to the formation of the 1H‐imidazoimidazole‐fused compounds. The transformation is postulated to proceed through an exclusive hyperiodonium‐mediated N‐Michael addition followed by N‐annulation cascade.

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The Aza-Wharton Reaction: Syntheses of Cyclic Allylic Amines and Vicinal Hydroxyamines from the Respective Acylaziridines

Abstract: The Wharton reaction, initially described for acyl epoxides, has been studied using the structurally similar aziridines. By this reaction, a range of cyclic allylic amines and vicinal amino alcohols have been prepared stereoselectively and, in some cases, enantiomerically pure.

Cited by 10 publications

References 18 publications

Hydrogen-Borrowing Amination of Secondary Alcohols Promoted by a (Cyclopentadienone)iron Complex

Hydrogen-Borrowing Amination of Secondary Alcohols Promoted by a (Cyclopentadienone)iron Complex

Recent Advances in the Chemistry of 2-Acylaziridines

Synthesis of Cyclohexenone(aryl)iodonium Salts and Their Application in Construction of Fused aza‐Heterocyclic Skeletons

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