Optically active cyclohex-3-en-1-one ketals by photolysis of N(3)CO(2)Et or N3C(OEt)NMs or by CaO induced alpha-elimination of NsONHCO(2)Et give diastereomeric aziridines (up to 72% yields, up to 60% d.e.). A simple HPLC separation allows to obtain practically pure aziridines. The conversion of the main product to the ketal of (R)-N-(ethoxycarbonyl)-beta-aminocyclohexanone is also reported and a further oxidation directly gives a derivative of(R)-2-aminoadipic acid. (C) 1997 Elsevier Science Ltd.
Stereoselectivity in the amination of chiral cyclohex-3-en-1-one ketals / Fioravanti, Stefania; Giuseppe, Luna; Pellacani, Lucio; Tardella, Paolo Antonio. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 53:13(1997), pp. 4779-4786. [10.1016/s0040-4020(97)00161-0]
Stereoselectivity in the amination of chiral cyclohex-3-en-1-one ketals
FIORAVANTI, Stefania;PELLACANI, Lucio;TARDELLA, Paolo Antonio
1997
Abstract
Optically active cyclohex-3-en-1-one ketals by photolysis of N(3)CO(2)Et or N3C(OEt)NMs or by CaO induced alpha-elimination of NsONHCO(2)Et give diastereomeric aziridines (up to 72% yields, up to 60% d.e.). A simple HPLC separation allows to obtain practically pure aziridines. The conversion of the main product to the ketal of (R)-N-(ethoxycarbonyl)-beta-aminocyclohexanone is also reported and a further oxidation directly gives a derivative of(R)-2-aminoadipic acid. (C) 1997 Elsevier Science Ltd.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
