Stereoselective access to trans-2,5-disubstituted pyrrolidine derivatives by nucleophilic addition to bicyclic N-acyliminium ion

DOI: 10.1016/S0040-4039(97)00099-3

Source and publish data:

Tetrahedron Letters p. 1415 - 1418 (1997)

Update date:2022-08-05

Topics:

Authors:

Dhimane, Hamid

Vanucci, Corinne

Lhommet, Gerard

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Article abstract of DOI:10.1016/S0040-4039(97)00099-3

5-Alkoxy-pyrroloxazolidin-3-ones 1 were stereoselectively prepared from (S)-pyroglutamic acid. Treatment of 1 with a Lewis acid generated in situ the N-acyliminium 2, which was trapped by various π-nuclcophiles leading selectively to trans pyrrolidine derivatives 3.

Full text of DOI:10.1016/S0040-4039(97)00099-3

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