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Issue 12, 2007
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Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidinesvia lithium amide conjugate addition

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Abstract

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 via β-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.

Graphical abstract: Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidinesvia lithium amide conjugate addition

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Submitted
02 Apr 2007
Accepted
08 May 2007
First published
17 May 2007

Org. Biomol. Chem., 2007,5, 1961-1969
Article type
Paper

Asymmetric synthesis of 3,4-anti- and 3,4-syn-substituted aminopyrrolidinesvia lithium amide conjugate addition

S. G. Davies, A. C. Garner, E. C. Goddard, D. Kruchinin, P. M. Roberts, A. D. Smith, H. Rodriguez-Solla, J. E. Thomson and S. M. Toms, Org. Biomol. Chem., 2007, 5, 1961
DOI: 10.1039/B704932C

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