Stereoselective azide cycloaddition to chiral cyclopentanone enamines

DOI: 10.1016/S0957-4166(97)00239-5

Source and publish data:

Tetrahedron Asymmetry p. 2261 - 2266 (1997)

Update date:2022-08-03

Topics:

Authors:

Fioravanti, Stefania

Pellacani, Lucio

Ricci, Damiano

Tardella, Paolo A.

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Article abstract of DOI:10.1016/S0957-4166(97)00239-5

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.

Full text of DOI:10.1016/S0957-4166(97)00239-5

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