Stereoselectivity in the amination of chiral cyclohex-3-en-1-one ketals
1997; Elsevier BV; Volume: 53; Issue: 13 Linguagem: Inglês
10.1016/s0040-4020(97)00161-0
ISSN1464-5416
AutoresStefania Fioravanti, Giuseppe Antonio Di Luna, Lucio Pellacani, Paolo A. Tardella,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoAbstract Optically active cyclohex-3-en-1-one ketals by photolysis of N 3 CO 2 Et or N 3 C(OEt)NMs or by CaO induced α-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)- β -aminocyclohexanone is also reported and a further oxidation directly gives a derivative of ( R )-2-aminoadipic acid.
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