2007
DOI: 10.1007/s10593-007-0028-7
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Unnatural amino acids. 3. Aziridinyl ketones from esters and amides of aziridine-2-carboxylic acids

Abstract: A series of N-substituted amides and esters of aziridine-2-carboxylic acids have been prepared and have been subjected to deprotonation with lithium diisopropylamide. The intermediate carbanions reacted more readily with the carbonyl groups of the substrates than with methyl iodide. So, in place of the expected amides or esters of methylaziridine-2-carboxylic acids, amides or esters of 2-aziridinylcarbonylaziridine-2-carboxylic acids were isolated.Keywords: aziridinyl ketones, esters and amides of aziridin-2-c… Show more

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Cited by 5 publications
(3 citation statements)
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“…Hydroxylamines 3b–f were synthesized from corresponding esters 1 as described in [ 12 ] or from activated bis-Boc amides 2 according to the published procedure [ 24 ]. Aziridine-2-carboxylic acid amides 4a and 4b were obtained from the aziridine-2-carboxylic acid dimethylamide in accordance with the previous reports [ 8 ]. All reactions involving organolithium compounds were carried out under an argon atmosphere.…”
Section: Methodssupporting
confidence: 86%
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“…Hydroxylamines 3b–f were synthesized from corresponding esters 1 as described in [ 12 ] or from activated bis-Boc amides 2 according to the published procedure [ 24 ]. Aziridine-2-carboxylic acid amides 4a and 4b were obtained from the aziridine-2-carboxylic acid dimethylamide in accordance with the previous reports [ 8 ]. All reactions involving organolithium compounds were carried out under an argon atmosphere.…”
Section: Methodssupporting
confidence: 86%
“…From our previous work [ 8 ], we knew that dimethyl amides 4a ( Scheme 2 ) and 4b (Scheme 4) were more readily available in comparison with Weinreb amides through direct aminolysis of corresponding methyl esters. In the synthesis of 2-aziridinylketones from N -protected N,N -dimethyl aziridine-2-carboxamides 4a,b as substrates, we have demonstrated comparable results in chemical yields and regioselectivity with the Weinreb amides described in the literature [ 11 , 12 , 13 ].…”
Section: Resultsmentioning
confidence: 99%
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