Back
Gold(i)-catalyzed stereoselective cyclization of 1,3-enyne aldehydes by a 1,3-acyloxy migration/Nazarov cyclization/aldol addition cascade.
Journal article

Gold(i)-catalyzed stereoselective cyclization of 1,3-enyne aldehydes by a 1,3-acyloxy migration/Nazarov cyclization/aldol addition cascade.

  • Brandstätter M Laboratorium für Organische Chemie, HCI H335 , Eidgenössische Technische Hochschule Zürich , Vladimir-Prelog-Weg 3 , 8093 Zürich , Switzerland . Email: carreira@org.chem.ethz.ch.
  • Huwyler N Laboratorium für Organische Chemie, HCI H335 , Eidgenössische Technische Hochschule Zürich , Vladimir-Prelog-Weg 3 , 8093 Zürich , Switzerland . Email: carreira@org.chem.ethz.ch.
  • Carreira EM Laboratorium für Organische Chemie, HCI H335 , Eidgenössische Technische Hochschule Zürich , Vladimir-Prelog-Weg 3 , 8093 Zürich , Switzerland . Email: carreira@org.chem.ethz.ch.
  • 2019-12-21
Published in:
  • Chemical science. - 2019
General Chemistry
English Stereoselective synthesis of bicyclo[3.3.0]octenones from chiral 1,3-enyne aldehydes bearing propargylic acetates is described. The method is based on a Au(i)-catalyzed domino sequence with concomitant transfer of chirality involving 1,3-acyloxy migration followed by Nazarov cyclization and an unprecedented aldol addition. The method furnishes densely functionalized bicyclic structures in high yields, with up to 97% ee and good diastereoselectivity.
Language
  • English
Open access status
gold
Identifiers
Persistent URL
https://sonar.ch/global/documents/189256
Statistics
Document views: 11 File downloads: