Scientific article

Organocatalyzed conjugate addition of carbonyl compounds to Nitrodienes/Nitroenynes and synthetic applications

Published inAdvanced synthesis & catalysis, vol. 352, no. 4, p. 667-695
Publication date2010

The purpose of this study is to point out the synthetic utility of a new class of Michael acceptors (nitrodienes and nitroenynes). The highly enantioselective organocatalytic Michael addition of carbonyl compounds to these functionalized nitroolefins has been carried out in the presence of (S)-diphenylprolinol silyl ether to achieve some interesting building blocks in high selectivities. The adducts thus obtained can be easily converted by taking advantage of the corresponding unsaturated carbon-carbon bond. In presence of the double bond, metathesis or electrophilic activation could be carried out whereas in the presence of the triple bond electrophilic activation could be conducted. We thus focused on a gold-catalyzed cyclization of the bis-homopropargylic alcohol to afford the corresponding substituted tetrahydrofuran. Then, we also demonstrated that organic and gold catalysts were compatible in a one-pot process. Indeed, we developed a one-pot enantioselective organocatalytic Michael addition to a nitroenyne followed by a gold-catalyzed acetalization/cyclization to achieve tetrahydrofuranyl ethers in high diastereo- and enantioselectivities with excellent yields.

  • Gold catalysis
  • Michael addition
  • Nitrodienes
  • One-pot procedure
  • Organocatalysis
Citation (ISO format)
BELOT, Sébastien et al. Organocatalyzed conjugate addition of carbonyl compounds to Nitrodienes/Nitroenynes and synthetic applications. In: Advanced synthesis & catalysis, 2010, vol. 352, n° 4, p. 667–695. doi: 10.1002/adsc.200900814
Main files (1)
Article (Published version)
ISSN of the journal1615-4150

Technical informations

Creation04/26/2010 10:00:00 AM
First validation04/26/2010 10:00:00 AM
Update time03/14/2023 3:28:15 PM
Status update03/14/2023 3:28:15 PM
Last indexation01/15/2024 7:54:09 PM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack