Synthesis of simple enantiopure tetrahydro-beta-carbolines and tetrahydroisoquinolines

Authors
Tietze, LF Zhou, YF Topken, E
Citation
Lf. Tietze et al., Synthesis of simple enantiopure tetrahydro-beta-carbolines and tetrahydroisoquinolines, EUR J ORG C, (12), 2000, pp. 2247-2252
Citations number
42
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
12
Year of publication
2000
Pages
2247 - 2252
Database
ISI
SICI code
1434-193X(200006):12<2247:SOSETA>2.0.ZU;2-V
Abstract
Enantioselective hydrogenation of the imines 11-13, 27 and 30 with the Ru c omplex (R,R)-5 led to the tetrahydro-beta-carbolines (1S)-14, (1R)-21 and ( 1S)-22, and the tetrahydroisoquinoline (1S)-31 with ee > 95%. By employing (S,S)-5 the enantiomers are accessible. The imines 11-12 and 27 were obtain ed by oxidation of racemic 14, 21 and 22 with KMnO4 in > 58% yield.