Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl eaters efficient precursors of (Z)-2,3-methanoamino acids

Citation
S. Racouchot et al., Titanium-mediated diastereoselective formation of (Z)-1-(1-alkenyl)-2-substituted-cyclopropyl eaters efficient precursors of (Z)-2,3-methanoamino acids, SYNLETT, (12), 2000, pp. 1729-1732
Citations number
34
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
12
Year of publication
2000
Pages
1729 - 1732
Database
ISI
SICI code
0936-5214(200012):12<1729:TDFO(>2.0.ZU;2-4
Abstract
The titanium-mediated cyclopropanation of homoallyl alk-2-enoates, emerged as the most convenient method to form diastereomerically pure (Z)-1-(1-alke nyl)-2-alkylcyclopropanols, precursors of significant 1,1-dimethyleneallylm etal species. Then, azidation of such complexes followed by a simple reduct ion-oxidation sequence provided diastereochemically pure (Z)-2,3-methanoami no acids.