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The diastereoselective conjugate addition of homochiral lithium amides to methyl 4-(N-allyl-N-benzylamino)but-2-enoate has been used as the key step in a simple and efficient protocol for the preparation of 3,4-substituted aminopyrrolidines. This protocol provides a complementary and stereoselective route to both anti- and syn-3-amino-4-alkylpyrrolidines as well as anti- and syn-3-hydroxy-4-aminopyrrolidines, in high de and ee viabeta-amino enolate functionalisation. This methodology has been applied to the synthesis of anti-(3S,4S)- and syn-(3R,4S)-3-methoxy-4-(N-methylamino)pyrrolidine.

Original publication

DOI

10.1039/b704932c

Type

Journal article

Journal

Org Biomol Chem

Publication Date

21/06/2007

Volume

5

Pages

1961 - 1969

Keywords

Amides, Lithium, Models, Molecular, Molecular Structure, Organometallic Compounds, Pyrrolidines, Stereoisomerism