Dual enantioselective control by heterocycles of (S)-indoline derivatives

Dual enantioselective control by heterocycles of (S)-indoline derivatives

Diastereo-and enantioselective pinacol coupling reactions of chiral α-ketoamides mediated by samarium diiodide afforded extremely high diastereoselectivities. Enantiopure ( )- or ( )-2,3-dialkyltartaric acid and derivatives can be synthesized. Diels-Alder cycloadditions of -indoline chiral acrylamid...

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Veröffentlicht in:Pure and applied chemistry 2005-12, Vol.77 (12), p.2053-2059
Hauptverfasser: Kim, Yong Hae, Jung, Doo Young, Youn, So Won, Kim, Sam Min, Park, Doo Han
Format: Artikel
Sprache:eng
Schlagworte:
Chemical reactions
Cyclopentadiene
Derivatives
Enantiomers
Enantioselective
Lewis acid
pinacol coupling
S-indoline
Samarium
samarium diiodide
Selectivity
α-ketoamides
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Zusammenfassung:Diastereo-and enantioselective pinacol coupling reactions of chiral α-ketoamides mediated by samarium diiodide afforded extremely high diastereoselectivities. Enantiopure ( )- or ( )-2,3-dialkyltartaric acid and derivatives can be synthesized. Diels-Alder cycloadditions of -indoline chiral acrylamides with cyclopentadiene in the presence of Lewis acids proceed with high diastereofacial selectivity, giving either or products depending on Lewis acid and the structures of chiral dienophiles.
ISSN:0033-4545
1365-3075
DOI:10.1351/pac200577122053