STEREOSELECTIVE AZIDE CYCLOADDITION TO CHIRAL CYCLOPENTANONE ENAMINES

Authors
FIORAVANTI S PELLACANI L RICCI D TARDELLA PA
Citation
S. Fioravanti et al., STEREOSELECTIVE AZIDE CYCLOADDITION TO CHIRAL CYCLOPENTANONE ENAMINES, Tetrahedron : asymmetry, 8(13), 1997, pp. 2261-2266
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
13
Year of publication
1997
Pages
2261 - 2266
Database
ISI
SICI code
0957-4166(1997)8:13<2261:SACTCC>2.0.ZU;2-3
Abstract
The enamine derived from cyclopentanone and (2R,5R)-2,5-bis(methoxymet hyl)pyrrolidine added ethyl N-mesylazidoformimidate [N3C(OEt)NMs] and ethyl azidoformate (N3CO2Et) with high asymmetric induction (>95%), wh ile the corresponding cyclohexanone enamine gave ring contraction prod ucts. With the same azides the cyclopentanone enamine, prepared from ( S)-2-(methoxymethyl)pyrrolidine gave N-substituted alpha-amino cyclope ntanones in moderate enantiomeric excess. (C) 1997 Elsevier Science Lt d.