Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction

Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction

An optically active tetrahydroquinoline intermediate (5) was prepared in 8 steps from monoprotected ethylene glycol, using a Pd-catalysed aza-Michael reaction to induce chirality. This can be transformed into three Galipea alkaloids (angustureine, galipeine and cuspareine). The proximity of a benzyl...

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Veröffentlicht in:Organic & biomolecular chemistry 2012-06, Vol.10 (22), p.4424-4432
Hauptverfasser: Taylor, Laura L, Goldberg, Frederick W, Hii, King Kuok Mimi
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
Aza Compounds - chemistry
Catalysis
Cyclization
Molecular Structure
Oxidation-Reduction
Palladium - chemistry
Quinolines - chemical synthesis
Rutaceae - chemistry
Stereoisomerism
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Zusammenfassung:An optically active tetrahydroquinoline intermediate (5) was prepared in 8 steps from monoprotected ethylene glycol, using a Pd-catalysed aza-Michael reaction to induce chirality. This can be transformed into three Galipea alkaloids (angustureine, galipeine and cuspareine). The proximity of a benzyloxy group is found to exert profound effects in several steps of the synthesis.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25122a