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Internal nucleophilic catalyst mediated cyclisation/ring expansion cascades for the synthesis of medium-sized lactones and lactams

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JournalAngewandte Chemie International Edition
DateAccepted/In press - 24 Jul 2019
DateE-pub ahead of print - 13 Aug 2019
DatePublished (current) - 24 Sep 2019
Issue number39
Volume58
Pages (from-to)13942-13947
Early online date13/08/19
Original languageEnglish

Abstract

A strategy for the synthesis of medium-sized lactones and lactams from linear precursors is described in which an amine acts as an internal nucleophilic catalyst to facilitate a novel cyclisation/ring expansion cascade sequence. This method obviates the need to use high-dilution conditions usually associated with medium-ring cyclisation protocols, as the reactions operate exclusively via kinetically favourable 'normal' sized cyclic transition states. This same feature also enables biaryl-containing medium-sized rings to be prepared with complete atroposelectivity via point-to-axial chirality transfer.

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© 2019 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

  • atropisomers, axial chirality, medium-sized rings, pyridines, ring expansion

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