Facile preparation of alpha-amino ketones from oxidative ring-opening of aziridines by pyridine N-oxide.
نویسندگان
چکیده
The oxidative ring-opening reaction of a variety of activated aziridines by pyridine N-oxide provided alpha-amino ketones or alpha-amino aldehydes in good yields.
منابع مشابه
Microwave-assisted regioselective ring opening of non-activated aziridines by lithium aluminium hydride.
A new synthetic protocol for the LiAlH(4)-promoted reduction of non-activated aziridines under microwave conditions was developed. Thus, ring opening of 2-(acetoxymethyl)aziridines provided the corresponding beta-amino alcohols, which were then used as eligible substrates in the synthesis of 5-methylmorpholin-2-ones via condensation with glyoxal in THF. The same procedure was applied for the pr...
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The asymmetric ring-opening of meso-aziridines with primary alcohols is realized using an N,N'-dioxide-Mg(OTf)2 complex as the catalyst. The desired vicinal trans-β-amino ethers are afforded in good yields and enantioselectivities. Aniline and water could also be used as the nucleophiles for the ring-opening in an identical catalyst system.
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The reactivity of dianions of carboxylic acids towards aziridines has been studied. Although, a similar reactivity to that of enolates from ketones, esters or amides has been observed, the method directly yields γ-aminoacids in one step. The method is complementary of previous results of enenediolate reactivity with other electrophiles. A comparative study with the reactivity of this enediolate...
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We report herein the synthesis of enantiomerically pure 2-phenyl- and 2-ethyl-2-trifluoromethylaziridines by Mitsunobu-type cyclisation of the corresponding N-protected amino alcohols, and our results regarding their ring opening with selected nucleophiles. Under basic conditions, N-tosyl aziridines have been regioselectively opened at the less hindered carbon. Under acidic conditions, the regi...
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عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 5 21 شماره
صفحات -
تاریخ انتشار 2007