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Gram-Scale Synthesis of the (-)-Sparteine Surrogate and (-)-Sparteine

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JournalAngewandte Chemie International Edition
DateAccepted/In press - 14 Nov 2017
DateE-pub ahead of print - 20 Nov 2017
DatePublished (current) - 2 Jan 2018
Issue number1
Volume57
Number of pages4
Pages (from-to)223-226
Early online date20/11/17
Original languageEnglish

Abstract

An 8-step, gram-scale synthesis of the (-)-sparteine surrogate (22% yield, with just 3 chromatographic purifications) and a 10-step, gram-scale synthesis of (-)-sparteine (31% yield) are reported. Both syntheses proceed with complete diastereocontrol and allow access to either antipode. Since the syntheses do not rely on natural product extraction, our work addresses long-term supply issues relating to these widely used chiral ligands.

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© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details

    Research areas

  • Journal Article, asymmetric synthesis, alkaloids, kinetic resolution, total synthesis, nitrogen ligands

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