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Highly diastereoselective nitrone cycloaddition onto a chiral ketene equivalent: asymmetric synthesis of cispentacin
Varinder K Aggarwal1, Stephen J Roseblade, Juliet K Barrell
1Department of Chemistry, University of Bristol, Cantock's Close, Bristol, and Celltech R+D Ltd, 216 Bath Road, Slough SL1 4EN, UK. v.aggarwal@bris.ac.uk
Organic Letters
|April 2, 2002
Abstract:
[reaction: see text] A highly diastereoselective intramolecular nitrone cycloaddition onto a chiral ketene equivalent, obtained by Horner-Wadsworth-Emmons olefination of either enantiomer of bis-sulfinyl phosphonate 6, is described. Cycloaddition gave 5,5-disubstituted isoxazolidine 10 in good yield as a single diastereomer. Catalytic hydrogenolysis of 10 furnished either enantiomer of optically pure cis-2-aminocyclopentane-1-carboxylic acid.