Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 39, Pages 13942-13947Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201907206
Keywords
atropisomers; axial chirality; medium-sized rings; pyridines; ring expansion
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Funding
- EPSRC [EP/P029795/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/P029795/1] Funding Source: Medline
- Leverhulme Trust [ECF-2015-013] Funding Source: Medline
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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 for the 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 by point-to-axial chirality transfer.
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