Tetrahedron Asymmetry p. 2261 - 2266 (1997)
Update date:2022-08-03
Topics:
Fioravanti, Stefania
Pellacani, Lucio
Ricci, Damiano
Tardella, Paolo A.
The enamine derived from cyclopentanone and (2R,5R)-2,5-bis(methoxymethyl )pyrrolidine added ethyl N-mesylazidoformimidate [N3C(OEt)NMs] and ethyl azidoformate (N3CO2Et) with high asymmetric induction (>95%), while the corresponding cyclohexanone enamine gave ring contraction products. With the same azides the cyclopentanone enamine, prepared from (S)-2-(methoxymethyl)pyrrolidine gave N-substituted α-amino cyclopentanones in moderate enantiomeric excess.
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