Selective reduction of acyl aziridines to Mannich bases using silyllithium reagents

Davis, Amanda L.; Korous, Arthur A.; Hartel, Aaron M.

doi:10.1016/j.tetlet.2013.05.005

Cited by 9 publications

(4 citation statements)

References 15 publications

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“…Selective reduction of 2-acylaziridines 127 using silyllithium reagent produces Mannich bases 132 (Scheme 29). 44 2-Pyrazolines 136 may be obtained in domino reaction of 2-acylaziridines 133 with the Huisgen zwitterions generated from dialkyl azodicarboxylates 134 and triphenylphos-phine in excellent yields (Scheme 30). 45 The proposed multistep mechanism starts with the nucleophilic addition of the zwitterion 135 to the carbonyl group of 133 to form 137, which subsequently cyclizes into oxadiazoline 138 along with elimination of triphenylphosphine oxide.…”

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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Section: Short Review Syn Thesismentioning

confidence: 99%

Recent Advances in the Chemistry of 2-Acylaziridines

Pankova

Кузнецов

2017

Synthesis

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“… 16 In a distinct and mechanistically different reaction, the addition of silyl anions to 2-aziridinyl ketones leads to β-amino ketones via an addition, Brook rearrangement, and anionic induced-ring opening. 17 …”

Section: Introductionmentioning

confidence: 99%

“…In a non-electron-transfer process, tributyltin hydride is known to open aziridinyl ketones to give β-amino ketones in a radical process . In a distinct and mechanistically different reaction, the addition of silyl anions to 2-aziridinyl ketones leads to β-amino ketones via an addition, Brook rearrangement, and anionic induced-ring opening …”

Section: Introductionmentioning

confidence: 99%

β-Amino Esters from the Reductive Ring Opening of Aziridine-2-carboxylates

Zhao

Wulff

2014

J. Org. Chem.

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A general study is undertaken to examine the scope of the reductive ring opening of aziridine-2-carboxylates with samarium diiodide. The competition between C–C and C–N bond cleavage is examined as a function of the nature of the N-substituent of the aziridine, the nature of the substituent in the 3-position of the aziridine, and whether the substituent in the 3-position is in a cis or trans relationship with the carboxylate in the 2-position. The desired C–N bond cleavage leads to β-amino esters that are the predominant products for most aziridines with an N-activating group. However, C–C cleavage products are observed with an aryl group in the 3-position; this can be particularly pronounced with cis-aziridines where a nearly equal mixture of the two is observed. Exclusive formation of the C–N cleavage product is observed for all aziridines with the strongly N-activating p-toluene sulfonate group. Similarly high selectivity is observed for the 2-trimethylsilylethyl sulfonate group (SES), which is easier to remove. The utility of these methods is illustrated in the synthesis of protected forms of (R)-β3-DOPA and l-DOPA from the same aziridine, the former by SmI2-mediated reductive opening at C-2 and the latter by palladium-mediated reductive opening at C-3.

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“…[3][4][5][6][7] Several methods are known for the synthesis of β-amino ketones from the ring opening of aziridines. A literature survey shows the few reducing agents, including Raney nickel in ethanol, 8 Pearlman's catalyst [Pd(OH) 2 /C], 9 Adam's catalyst (PtO 2 /HCO 2 H), 10 sodium borohydride, 11 tributyltin hydride, 12 poly(methylhydrosiloxane) (PMHS), 13 silyllithium reagents, 14 magnesium 15 and lithium 16 metal reagents, titanium tetraiodide, 17 samarium(II) iodide 18 and visible-light photoredox ruthenium catalysts, 19 for the reductive ring opening of aziridines. None of these methods, however, result in a direct reduction reaction of N-H aziridines to give derivatives of β-carbamato ketones.…”

mentioning

confidence: 99%

Synthesis of tert-Butyl 1,3-Diaryl-3-oxopropylcarbamates by a Regiocontrolled Reduction of Ketoaziridines

Samimi

Yamin²,

Saberi

2014

Synthesis

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A new, convenient approach for the reductive ring opening of N-H ketoaziridines is described. Treatment of N-H ketoaziridines with di-tert-butyl dicarbonate [(Boc) 2 O] in the presence of sodium iodide and nickel(II) chloride results in the corresponding tert-butyl 1,3-diaryl-3-oxopropylcarbamates by a regiocontrolled reaction. The structure of the regioisomeric product was confirmed by X-ray crystal structure analysis.

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Selective reduction of acyl aziridines to Mannich bases using silyllithium reagents

Cited by 9 publications

References 15 publications

Recent Advances in the Chemistry of 2-Acylaziridines

Recent Advances in the Chemistry of 2-Acylaziridines

β-Amino Esters from the Reductive Ring Opening of Aziridine-2-carboxylates

Synthesis of tert-Butyl 1,3-Diaryl-3-oxopropylcarbamates by a Regiocontrolled Reduction of Ketoaziridines

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