Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2005, Issue 13, Pages 2689-2693Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200500095
Keywords
alkaloids; alkynes; asymmetric synthesis; hydroamination; titanium
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The study presents a new pathway for the enantioselective synthesis of benzylisoquinoline alkaloids. The key steps of the synthesis of (+)-(S)-laudanosine (1) and (-)-(S)-xylopinine (2) are a Sonogashira coupling that builds up the C1-C8a bond of the benzylisoquinoline skeleton, an intramolecular Ti-catalyzed hydroamination of an alkyne, and a subsequent enantioselective imine reduction according to Noyori's protocol. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).
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