Aziridino ketones

Dicobalt octacarbonyl in anhydrous acetonitrile promoted the rearrangement of 4-isoxazolines to isomeric 2-acylaziridines with yields ranging from 39 to 92%. The optically pure isoxazoline 64 underwent a totally d iastereoselective rearrangement to give aziridino ketone 65 as a single isomer <020L1907>. 

Various enantiomerically pure aziridino ketones, e.g. 1814, have been prepared from the corresponding secondary alcohols 1813 by Swern oxidation. The configurationally stable a-amino ketones were stereoselectively reduced by L-Sdectride to provide the corresponding alcohols with high diastereoselectivities and in high... 

Enantioselective addition of diethylzinc to benzaldehyde has been promoted by indole-containing chiral oxazolidines (which are able to use both O and N atoms to effect metal coordination in the transition state), and by chiral o-hydroxyphenyl diaza-phospholidine oxide,and by chiral aziridino alcohols.Enantioselective addition of dialkylzinc to prostereogenic ketones has been promoted using chiral camphorsul-fonamide derivatives. 

Propan 2-Aziridino-hexafluor-2-hydroxy- E14a/2, 66 (Keton/Amin)... 

Oxiran 2-Aziridino-3,3-dimethyl-2-phenyl- E14a/2, 382 (2-Brom-keton/Aziridin)... 

Only one example was found where this class of amino acids was produced. Oxidation of 7.246 gave a ketone and treatment with boron trifluoride led to the conjugated ketone, 7.247.132 Conjugate addition of azide, reduction to the amine and cyclization gave diastereomeric methyl 9-(3-hexyl-2-aziridino)nonanoic acid (J.248 and 7.249). The final step in that sequence proceeded in only 37% yield. If the alkenyl moiety was converted to an epoxide moiety, aziridine carboxylic acids were prepared in good yield, via the azide.132... 

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