Jump to main content
Jump to site search

Issue 19, 2004
Previous Article Next Article

Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid

Author affiliations

Abstract

The diastereoselective conjugate addition of lithium (S)-N-benzyl-N-α-methylbenzylamide has been successfully applied to the first asymmetric syntheses of cis-(3S,4R)- and trans-(3R,4R)-4-aminotetrahydrofuran-3-carboxylic acids (26% and 25% overall yield respectively, >98% d.e. and >97% e.e. in each case). Furthermore, the most efficient asymmetric synthesis to date of cis-(3R,4R)- and trans-(3R,4S)-4-aminopyrrolidine carboxylic acids is delineated: for cis-(3R,4R), four steps, >98% d.e., 52% overall yield; for trans-(3R,4S), five steps, >98% d.e., 50% overall yield.

Graphical abstract: Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid

Back to tab navigation

Publication details

The article was received on 19 May 2004, accepted on 28 Jul 2004 and first published on 01 Sep 2004


Article type: Paper
DOI: 10.1039/B407558G
Citation: Org. Biomol. Chem., 2004,2, 2763-2776
  •   Request permissions

    Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid

    M. E. Bunnage, S. G. Davies, P. M. Roberts, A. D. Smith and J. M. Withey, Org. Biomol. Chem., 2004, 2, 2763
    DOI: 10.1039/B407558G

Search articles by author

Spotlight

Advertisements