Abstract
[GRAPHICS]
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.
Translated title of the contribution | 'Highly diastereoselective nitrone cycloaddition onto a chiral ketene equivalent: Asymmetric synthesis of cispentacin' |
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Original language | English |
Pages (from-to) | 1227-1229 |
Number of pages | 3 |
Journal | Organic Letters |
Volume | 4 |
Issue number | 7 |
DOIs | |
Publication status | Published - 12 Mar 2002 |
Keywords
- 1,3-DIPOLAR CYCLOADDITION
- (1R,3R)-2-METHYLENE-1,3-DITHIOLANE 1,3-DIOXIDE
- TRANS-1,3-DITHIANE 1,3-DIOXIDE
- PHYSICOCHEMICAL PROPERTIES
- SULFOXIDES
- OXIDATION
- FR109615
- OXAZABOROLIDINES
- STRATEGY