American Chemical Society
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Diastereoselective Intramolecular α-Amidoalkylation Reactions of l-DOPA Derivatives. Asymmetric Synthesis of Pyrrolo[2,1-a]isoquinolines

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journal contribution
posted on 2005-12-09, 00:00 authored by Eva García, Sonia Arrasate, Esther Lete, Nuria Sotomayor
Stereocontrolled intramolecular α-amidoalkylation reactions of l-DOPA-derived succinimides have been studied. Addition of MeLi to nonracemic succinimides 9ad yields oxoamides, which are cyclized upon treatment with Lewis or protic acids to afford (5S,10bS)-trans 11 or (5S,10bR)-cis 12 pyrroloisoquinolines with variable diastereoselectivities, but with high enantiomerical purities (ee 99%).