Diastereoselective intramolecular alpha-amidoalkylation reactions of L-DOPA derivatives. Asymmetric synthesis of pyrrolo[2,1-a]isoquinolines |
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| Authors: | García Eva Arrasate Sonia Lete Esther Sotomayor Nuria |
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| Institution: | Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea, Apdo 644, 48080 Bilbao, Spain. |
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| Abstract: | reaction: see text] Stereocontrolled intramolecular alpha-amidoalkylation reactions of L-DOPA-derived succinimides have been studied. Addition of MeLi to nonracemic succinimides 9a-d yields oxoamides, which are cyclized upon treatment with Lewis or protic acids to afford (5S,10bS)-trans 11 or (5S,10bR)-cis 12pyrroloisoquinolines with variable diastereoselectivities, but with high enantiomerical purities (ee 99%). |
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