STEREOSELECTIVITY IN THE AMINATION OF CHIRAL CYCLOHEX-3-EN-1-ONE KETALS

Authors
FIORAVANTI S LUNA G PELLACANI L TARDELLA PA
Citation
S. Fioravanti et al., STEREOSELECTIVITY IN THE AMINATION OF CHIRAL CYCLOHEX-3-EN-1-ONE KETALS, Tetrahedron, 53(13), 1997, pp. 4779-4786
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
13
Year of publication
1997
Pages
4779 - 4786
Database
ISI
SICI code
0040-4020(1997)53:13<4779:SITAOC>2.0.ZU;2-1
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 s imple HPLC separation allows to obtain practically pure aziridines. Th e conversion of the main product to the ketal of (R)-N-(ethoxycarbonyl )-beta-aminocyclohexanone is also reported and a further oxidation dir ectly gives a derivative of(R)-2-aminoadipic acid. (C) 1997 Elsevier S cience Ltd.