- Enantiopure trans -3-arylaziridine-2-carboxamides: Preparation by bacterial hydrolysis and ring-openings toward enantiopure, unnatural D -α-amino acids
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Several racemic trans-3-arylaziridine-2-carboxamides were prepared and then resolved by Rhodococcus rhodochrous IFO 15564-catalyzed hydrolysis. The resulting enantiopure (2R,3S)-3-arylaziridine-2-carboxamides are adequate substrates to undergo fully stereoselective nucleophilic ring-openings at the C-3 ring position to finally yield enantiopure, unnatural d-α- aminocarboxylic acids. Experimental evidence is provided that suggests the fate of the (2S,3R)-3-arylaziridine-2-carboxylic acids concomitantly formed during the resolution processes. In this context, the similar bacterial resolution of racemic 1-arylaziridine-2-carboxamides and -carbonitriles, previously investigated by our research group, has been partially re-examined.
- Moran-Ramallal, Roberto,Liz, Ramon,Gotor, Vicente
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supporting information; experimental part
p. 6614 - 6624
(2010/11/17)
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- Synthesis of α-Halocinnamate Esters via Solvolytic Rearrangement of Trichloroallyl Alcohols
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Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-α-chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement.Micharl addition of ammonia to these ester derivatives affords cis- and/or trans-aziridine amides.The facile rearrangement allows the synthesis of d,l-phenylalanine derived from perchloroethylene and toluene.
- Kruper, William J.,Emmons, Albert H.
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p. 3323 - 3329
(2007/10/02)
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- Reaction of Hydrogen Fluoride in Pyridine Solution with cis-Cyano-2- and cis-Amido-2-aziridines. Preparation of β-Fluoro-α-amino Acids and Esters by Means of Acidic Hydrolysis and Alcoholysis of β-Fluoro-α-Amino Nitriles and/or β-Fluoro-α-Amino Acid Amide
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The addition of hydrogen fluoride generated from pyridinium poly(hydrogen fluoride) (i.e.Olah's reagent) to some cis-2-cyano- and cis-2-amido-aziridines has been examined.The reaction led to fluoroamine derivatives which upon acidic hydrolysis and alcohol
- Ayi, Ayicoue I.,Guedj, Roger
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p. 2045 - 2051
(2007/10/02)
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