Dual enantioselective control by heterocycles of (S)-indoline derivatives
Diastereo-and enantioselective pinacol coupling reactions of chiral alpha-ketoamides mediated by samarium diiodide afforded extremely high diastereoselectivities. Enantiopure (S,S)- or (R,R)-2,3-dialkyltartaric acid and derivatives call be synthesized, Diels-Alder cycloadditions of S-indoline chiral acrylamides with cyclopentadiene in the presence of Lewis acids proceed with high diastereofacial selectivity, giving either endo-R or endo-S products depending on Lewis acid and the Structures of chiral dienophiles.
- Publisher
- INT UNION PURE APPLIED CHEMISTRY
- Issue Date
- 2005-12
- Language
- English
- Article Type
- Article; Proceedings Paper
- Keywords
CATALYTIC ASYMMETRIC INDUCTION; CHIRAL OXAZABOROLIDINES; BORANE REDUCTION; AMINO-ALCOHOLS; DIELS-ALDER; ALDEHYDES; KETONES; DIALKYLZINCS; MECHANISM; REAGENTS
- Citation
PURE AND APPLIED CHEMISTRY, v.77, no.12, pp.2053 - 2059
- ISSN
- 0033-4545
- Appears in Collection
- Files in This Item
- There are no files associated with this item.
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